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CAS 3019-71-4
2,2,2-Trichloro-N-(oxomethylidene)acetamideTrichloroacetylisocyanate
Codes: (VIII)270899-3-a, Cefcamate Pivoxil Hydrochloride-009
Application context (from source-drug indications)
Major depressive disorderEsketamine HydrochlorideSuicidal ideationEsketamine HydrochlorideDepressive disorderEsketamine HydrochlorideAnaesthesiaEsketamine HydrochlorideTreatment-resistant depressionEsketamine HydrochloridePainEsketamine HydrochlorideBacterial infectionCefcamate Pivoxil Hydrochloride
Source drugs (routes using this intermediate)
| Drug | Tier | Expiry |
|---|---|---|
| Esketamine Hydrochloride | Tier B — Position early | 2029 |
| Cefcamate Pivoxil Hydrochloride | 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.
2-Hydroxycyclohex-2-en-1-one→3-Bromo-2-hydroxycyclohex-2-en-1-one→3-Bromo-2-methoxycyclohex-2-en-1-one→2-Methoxycyclohex-2-en-1-one→(o-Chlorophenyl)boronic acid→2'-Chloro-2-methoxy-5,6-dihydro[1,1'-biphenyl]-3(4H)-one→(3S)-2'-Chloro-2-methoxy-3,4,5,6-tetrahydro[1,1'-biphenyl]-3-ol→2,2,2-Trichloro-N-(oxomethylidene)acetamide→(3S)-2'-Chloro-2-methoxy-3,4,5,6-tetrahydro[1,1'-biphenyl]-3-yl carbamate→(1S)-2'-Chloro-1-isocyanato-6-methoxy-1,2,3,4-tetrahydro-1,1'-biphenyl→(1S)-2'-Chloro-6-methoxy-N-methyl-3,4-dihydro[1,1'-biphenyl]-1(2H)-amine
Cefcamate Pivoxil HydrochlorideOptimised routesteps: 7total yield: 120.1g(Cefcamate Pivoxil Hydrochloride (API))
Ethyl2-(bromoacetyl)pent-2-enoate→tert-Butylcarbamothioylcarbamatehydrobromide→Ethyl(2Z)-2-[2-[(tert-butoxycarbonyl)amino]-1,3-thiazol-4-yl]pent-2-enoate→2-[2(Z)-2-Boc-amino-1,3-thiazol-4-yl]pent-2-enoicacid→(6R,7R)-7-Amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid→(6R,7R)-7-[[(2Z)-2-[2-[(tert-Butoxycarbonyl)amino]-1,3-thiazol-4-yl]pent-2-enoyl]amino]-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacidN,N,N',N'-tetramethylguanidine(11)→(6R,7R)-7-[[(2Z)-2-[2-[(tert-Butoxycarbonyl)amino]-1,3-thiazol-4-yl]pent-2-enoyl]amino]-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid→Chlorosulfonicacidisocyanate→Trichloroacetylisocyanate→(6R,7R)-7-[[(2Z)-2-[2-[(tert-Butoxycarbonyl)amino]-1,3-thiazol-4-yl]pent-2-enoyl]amino]-3-[(carbamoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacidN-(propan-2-yl)propan-2-amine→Sodium(6R,7R)-7-[[(2Z)-2-[2-[(tert-butoxycarbonyl)amino]-1,3-thiazol-4-yl]pent-2-enoyl]amino]-3-[(carbamoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate→(6R,7R)-7-[[(2Z)-2-[2-[(tert-Butoxycarbonyl)amino]-1,3-thiazol-4-yl]pent-2-enoyl]amino]-3-[(carbamoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid→(6R,7R)-7-[(Z)-2-(2-Aminothiazol-4-yl)-2-pentenoylamino]-3-(carbamoyloxymethyl)-3-cephem-4-carboxylicacid→(6R,7R)-7-[[(2Z)-2-(2-Amino-1,3-thiazol-4-yl)pent-2-enoyl]amino]-3-[(carbamoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacidhydrogenchloride→Iodomethylpivalate→[(2,2-Dimethylpropanoyl)oxy]methyl(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)pent-2-enoyl]amino]-3-[(carbamoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
Intermediates available on this site
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