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CAS 78-95-5
Chloroacetyl chloride
Codes: Imipenem-020, Tenofovir disoproxil phosphate-001
Application context (from source-drug indications)
Bacterial pneumoniaCilastatin Sodium/Imipenem/RelebactamHospital-acquired pneumoniaCilastatin Sodium/Imipenem/RelebactamInfectious diseaseCilastatin Sodium/Imipenem/RelebactamBacteraemiaCilastatin Sodium/Imipenem/RelebactamVentilator-associated pneumoniaCilastatin Sodium/Imipenem/RelebactamHealthcare-associated pneumoniaCilastatin Sodium/Imipenem/RelebactamHIV infectionLamivudine/Tenofovir Disoproxil FumarateChronic hepatitis BLamivudine/Tenofovir Disoproxil FumarateHIV infectionEfavirenz/Lamivudine/Tenofovir Disoproxil FumarateHIV infectionEmtricitabine/Rilpivirine Hydrochloride/Tenofovir Disoproxil FumarateHepatitis BTenofovir disoproxil phosphateBacterial infectionImipenemGonorrhoeaImipenemBacillus anthracis infectionImipenem
Source drugs (routes using this intermediate)
| Drug | Tier | Expiry |
|---|---|---|
| Cilastatin Sodium/Imipenem/Relebactam | Tier C — Watch / trade | - |
| Lamivudine/Tenofovir Disoproxil Fumarate | Tier C — Watch / trade | - |
| Efavirenz/Lamivudine/Tenofovir Disoproxil Fumarate | Tier C — Watch / trade | - |
| Emtricitabine/Rilpivirine Hydrochloride/Tenofovir Disoproxil Fumarate | Tier B — Position early | - |
| Tenofovir disoproxil phosphate | Tier C — Watch / trade | - |
| Imipenem | Tier C — Watch / trade | - |
Position in synthesis routes (up/downstream chain)
Ordered by route registration; left → right is the synthesis direction. The highlighted node is the current CAS; others link to their own profiles.
4-Methoxyphenylamine→1-Amino-4-fluorobenzene→4-Bromophenylamine→4-Ethoxyphenylamine→omega-Bromoacetophenone→Chloroacetyl chloride→2-Iodo-1-(3-methoxyphenyl)ethanone→1-Bromo-3,3-dimethylbutan-2-one<-fgf->→2-[(4-Methoxyphenyl)amino]-1-phenylethanone→1-[(4-Methoxyphenyl)amino]acetone→1-[(4-Fluorophenyl)amino]acetone→2-[(4-Bromophenyl)amino]-1-(3-methoxyphenyl)ethanone→1-[(4-Ethoxyphenyl)amino]-3,3-dimethylbutan-2-one→(3S)-4-Benzoyl-3-[(1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl]-1-(4-methoxyphenyl)azetidin-2-one→(3S)-4-Acetyl-3-[(1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl]-1-(4-methoxyphenyl)azetidin-2-one→(3S)-4-Acetyl-3-[(1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl]-1-(4-fluorophenyl)azetidin-2-one→(3S)-1-(4-Bromophenyl)-3-[(1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl]-4-(3-methoxybenzoyl)azetidin-2-one→(3S)-3-[(1R)-1-[[tert-Butyl(dimethyl)silyl]oxy]ethyl]-4-(2,2-dimethylpropanoyl)-1-(4-ethoxyphenyl)azetidin-2-one→(2R,3R)-3-Methyloxirane-2-carboxylic acid→L-Threonine→(2R,3R)-N-(4-Methoxyphenyl)-3-methyl-N-(2-oxo-2-phenylethyl)oxirane-2-carboxamide→(2R,3R)-N-(4-Methoxyphenyl)-3-methyl-N-(2-oxopropyl)oxirane-2-carboxamide→(2R,3R)-N-(4-Fluorophenyl)-3-methyl-N-(2-oxopropyl)oxirane-2-carboxamide→(2R,3R)-N-(4-Bromophenyl)-N-[2-(3-methoxyphenyl)-2-oxoethyl]-3-methyloxirane-2-carboxamide→(2R,3R)-N-(3,3-Dimethyl-2-oxobutyl)-N-(4-ethoxyphenyl)-3-methyloxirane-2-carboxamide→(3S)-4-Benzoyl-3-[(1R)-1-hydroxyethyl]-1-(4-methoxyphenyl)azetidin-2-one→(3S)-4-Acetyl-3-[(1R)-1-hydroxyethyl]-1-(4-methoxyphenyl)azetidin-2-one→(3S)-4-Acetyl-1-(4-fluorophenyl)-3-[(1R)-1-hydroxyethyl]azetidin-2-one→(3S)-1-(4-Bromophenyl)-3-[(1R)-1-hydroxyethyl]-4-(3-methoxybenzoyl)azetidin-2-one→(3S)-4-(2,2-Dimethylpropanoyl)-1-(4-ethoxyphenyl)-3-[(1R)-1-hydroxyethyl]azetidin-2-one→(1E)-1-[(4-Methoxyphenyl)imino]acetone→S-Pyridin-2-yl (3R)-3-[[tert-butyl(dimethyl)silyl]oxy]butanethioate→(2R,3R)-3-[(1R)-1-[[tert-Butyl(dimethyl)silyl]oxy]ethyl]-1-(4-methoxyphenyl)-4-oxoazetidin-2-yl acetate→(2R,3R)-3-[(1R)-1-[[tert-Butyl(dimethyl)silyl]oxy]ethyl]-1-(4-fluorophenyl)-4-oxoazetidin-2-yl acetate→(2R,3R)-1-(4-Bromophenyl)-3-[(1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl]-4-oxoazetidin-2-yl acetate→(2R,3R)-3-[(1R)-1-[[tert-Butyl(dimethyl)silyl]oxy]ethyl]-1-(4-ethoxyphenyl)-4-oxoazetidin-2-yl acetate→(2S,3S)-3-[(1R)-1-[[tert-Butyl(dimethyl)silyl]oxy]ethyl]-1-(4-methoxyphenyl)-4-oxoazetidine-2-carboxylic acid→(2R,3R)-3-[(1R)-1-[[tert-Butyl(dimethyl)silyl]oxy]ethyl]-4-oxoazetidin-2-yl acetate
Lamivudine/Tenofovir Disoproxil FumarateOptimised routesteps: 11total yield: 23.3g(Tenofovir disoproxil phosphate (API))
Chloroacetyl chloride→1-Chloro-2(R)-propanol→Diethyl (tosyloxy)methylphosphonate→Diethyl (chloromethyl)phosphonate→Diethyl phosphonate→Diethyl phosphonomethanol→Diethyl (2-chloro-1(R)-methylethoxy)methylphosphonate→6-Aminopurine→(R)-9-[2-(Diethylphosphonomethoxy)propyl] adenine→(R)-9-(2-Phosphonomethoxypropyl)adenine→Chloromethyl isopropyl carbonate→Bis[[(isopropoxycarbonyl)oxy]methyl] ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate→2(R)-Methyloxirane→(R)-(+)-9-(2-Hydroxypropyl)adenine→(R)-Propylene carbonate→(S)-Glycidol→(R)-1,2-Propanediol
Efavirenz/Lamivudine/Tenofovir Disoproxil FumarateOptimised routesteps: 11total yield: 23.3g(Tenofovir disoproxil phosphate (API))
Chloroacetyl chloride→1-Chloro-2(R)-propanol→Diethyl (tosyloxy)methylphosphonate→Diethyl (chloromethyl)phosphonate→Diethyl phosphonate→Diethyl phosphonomethanol→Diethyl (2-chloro-1(R)-methylethoxy)methylphosphonate→6-Aminopurine→(R)-9-[2-(Diethylphosphonomethoxy)propyl] adenine→(R)-9-(2-Phosphonomethoxypropyl)adenine→Chloromethyl isopropyl carbonate→Bis[[(isopropoxycarbonyl)oxy]methyl] ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate→2(R)-Methyloxirane→(R)-(+)-9-(2-Hydroxypropyl)adenine→(R)-Propylene carbonate→(S)-Glycidol→(R)-1,2-Propanediol
Emtricitabine/Rilpivirine Hydrochloride/Tenofovir Disoproxil FumarateOptimised routesteps: 11total yield: 23.3g(Tenofovir disoproxil phosphate (API))
Chloroacetyl chloride→1-Chloro-2(R)-propanol→Diethyl (tosyloxy)methylphosphonate→Diethyl (chloromethyl)phosphonate→Diethyl phosphonate→Diethyl phosphonomethanol→Diethyl (2-chloro-1(R)-methylethoxy)methylphosphonate→6-Aminopurine→(R)-9-[2-(Diethylphosphonomethoxy)propyl] adenine→(R)-9-(2-Phosphonomethoxypropyl)adenine→Chloromethyl isopropyl carbonate→Bis[[(isopropoxycarbonyl)oxy]methyl] ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate→2(R)-Methyloxirane→(R)-(+)-9-(2-Hydroxypropyl)adenine→(R)-Propylene carbonate→(S)-Glycidol→(R)-1,2-Propanediol
Tenofovir disoproxil phosphateOptimised routesteps: 11total yield: 23.3g(Tenofovir disoproxil phosphate (API))
Chloroacetyl chloride→1-Chloro-2(R)-propanol→Diethyl (tosyloxy)methylphosphonate→Diethyl (chloromethyl)phosphonate→Diethyl phosphonate→Diethyl phosphonomethanol→Diethyl (2-chloro-1(R)-methylethoxy)methylphosphonate→6-Aminopurine→(R)-9-[2-(Diethylphosphonomethoxy)propyl] adenine→(R)-9-(2-Phosphonomethoxypropyl)adenine→Chloromethyl isopropyl carbonate→Bis[[(isopropoxycarbonyl)oxy]methyl] ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate→2(R)-Methyloxirane→(R)-(+)-9-(2-Hydroxypropyl)adenine→(R)-Propylene carbonate→(S)-Glycidol→(R)-1,2-Propanediol
4-Methoxyphenylamine→1-Amino-4-fluorobenzene→4-Bromophenylamine→4-Ethoxyphenylamine→omega-Bromoacetophenone→Chloroacetyl chloride→2-Iodo-1-(3-methoxyphenyl)ethanone→1-Bromo-3,3-dimethylbutan-2-one<-fgf->→2-[(4-Methoxyphenyl)amino]-1-phenylethanone→1-[(4-Methoxyphenyl)amino]acetone→1-[(4-Fluorophenyl)amino]acetone→2-[(4-Bromophenyl)amino]-1-(3-methoxyphenyl)ethanone→1-[(4-Ethoxyphenyl)amino]-3,3-dimethylbutan-2-one→(3S)-4-Benzoyl-3-[(1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl]-1-(4-methoxyphenyl)azetidin-2-one→(3S)-4-Acetyl-3-[(1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl]-1-(4-methoxyphenyl)azetidin-2-one→(3S)-4-Acetyl-3-[(1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl]-1-(4-fluorophenyl)azetidin-2-one→(3S)-1-(4-Bromophenyl)-3-[(1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl]-4-(3-methoxybenzoyl)azetidin-2-one→(3S)-3-[(1R)-1-[[tert-Butyl(dimethyl)silyl]oxy]ethyl]-4-(2,2-dimethylpropanoyl)-1-(4-ethoxyphenyl)azetidin-2-one→(2R,3R)-3-Methyloxirane-2-carboxylic acid→L-Threonine→(2R,3R)-N-(4-Methoxyphenyl)-3-methyl-N-(2-oxo-2-phenylethyl)oxirane-2-carboxamide→(2R,3R)-N-(4-Methoxyphenyl)-3-methyl-N-(2-oxopropyl)oxirane-2-carboxamide→(2R,3R)-N-(4-Fluorophenyl)-3-methyl-N-(2-oxopropyl)oxirane-2-carboxamide→(2R,3R)-N-(4-Bromophenyl)-N-[2-(3-methoxyphenyl)-2-oxoethyl]-3-methyloxirane-2-carboxamide→(2R,3R)-N-(3,3-Dimethyl-2-oxobutyl)-N-(4-ethoxyphenyl)-3-methyloxirane-2-carboxamide→(3S)-4-Benzoyl-3-[(1R)-1-hydroxyethyl]-1-(4-methoxyphenyl)azetidin-2-one→(3S)-4-Acetyl-3-[(1R)-1-hydroxyethyl]-1-(4-methoxyphenyl)azetidin-2-one→(3S)-4-Acetyl-1-(4-fluorophenyl)-3-[(1R)-1-hydroxyethyl]azetidin-2-one→(3S)-1-(4-Bromophenyl)-3-[(1R)-1-hydroxyethyl]-4-(3-methoxybenzoyl)azetidin-2-one→(3S)-4-(2,2-Dimethylpropanoyl)-1-(4-ethoxyphenyl)-3-[(1R)-1-hydroxyethyl]azetidin-2-one→(1E)-1-[(4-Methoxyphenyl)imino]acetone→S-Pyridin-2-yl (3R)-3-[[tert-butyl(dimethyl)silyl]oxy]butanethioate→(2R,3R)-3-[(1R)-1-[[tert-Butyl(dimethyl)silyl]oxy]ethyl]-1-(4-methoxyphenyl)-4-oxoazetidin-2-yl acetate→(2R,3R)-3-[(1R)-1-[[tert-Butyl(dimethyl)silyl]oxy]ethyl]-1-(4-fluorophenyl)-4-oxoazetidin-2-yl acetate→(2R,3R)-1-(4-Bromophenyl)-3-[(1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl]-4-oxoazetidin-2-yl acetate→(2R,3R)-3-[(1R)-1-[[tert-Butyl(dimethyl)silyl]oxy]ethyl]-1-(4-ethoxyphenyl)-4-oxoazetidin-2-yl acetate→(2S,3S)-3-[(1R)-1-[[tert-Butyl(dimethyl)silyl]oxy]ethyl]-1-(4-methoxyphenyl)-4-oxoazetidine-2-carboxylic acid→(2R,3R)-3-[(1R)-1-[[tert-Butyl(dimethyl)silyl]oxy]ethyl]-4-oxoazetidin-2-yl acetate
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