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CAS 1120365-56-1

(6R,7R)-3-[[5-Amino-1-(2-hydroxyethyl)-1H-pyrazol-2-ium-2-yl]methyl]-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Codes: Cefoselis Sulfate-008

Application context (from source-drug indications)

Bacterial infectionCefoselis Sulfate

Source drugs (routes using this intermediate)

DrugTierExpiry
Cefoselis SulfateTier 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.

Cefoselis SulfateOptimised routesteps: 7total yield: 6.53g(Cefoselis Sulfate (API))
2-(5-Amino-1H-pyrazol-1-yl)ethan-1-ol→2-[5-(Formylamino)-1H-pyrazol-1-yl]ethyl formate→Diphenylmethyl (6R,7R)-7-[(tert-butoxycarbonyl)amino]-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate→2-([(6R,7R)-7-[(tert-Butoxycarbonyl)amino]-2-[(diphenylmethoxy)carbonyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl)-5-(formylamino)-1-[2-(formyloxy)ethyl]-1H-pyrazol-2-ium iodide→(6R,7R)-7-Amino-3-[[5-amino-1-(2-hydroxyethyl)-1H-pyrazol-2-ium-2-yl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate hydrochloride→(2Z)-[2-(Formylamino)-1,3-thiazol-4-yl](methoxyimino)ethanoic acid→(6R,7R)-3-[[5-Amino-1-(2-hydroxyethyl)-1H-pyrazol-2-ium-2-yl]methyl]-7-[[(2Z)-2-[2-(formylamino)-1,3-thiazol-4-yl]-2-(methoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate→(6R,7R)-3-[[5-Amino-1-(2-hydroxyethyl)-1H-pyrazol-2-ium-2-yl]methyl]-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate→1-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]-3-oxido-1H-1,2,3-benzotriazol-3-ium
Cefoselis SulfateOptimised routesteps: 3total yield: 2.18g(Cefoselis Sulfate (API))
4-Chloro-2(Z)-(methoxyimino)-3-oxobutyric acid→5-amino-2-{[(6R,7R)-7-amino-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-1-(2-hydroxyethyl)-1H-pyrazol-2-ium→3-amino-1-{[(6R,7R)-2-carboxylato-7-[(2Z)-4-chloro-2-(methoxyimino)-3-oxobutanamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-2-(2-hydroxyethyl)-2H-pyrazol-1-ium→Sulfourea→(6R,7R)-3-[[5-Amino-1-(2-hydroxyethyl)-1H-pyrazol-2-ium-2-yl]methyl]-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
Cefoselis SulfateOptimised routesteps: 4total yield: 117g(Cefoselis Sulfate (FREE))
(6R,7R)-3-(Acetoxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid→Trimethylsilyl (6R,7R)-3-(iodomethyl)-8-oxo-7-[(trimethylsilyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate→2-[5-(Formylamino)-1H-pyrazol-1-yl]ethyl formate→(6R,7R)-7-Amino-3-[[5-amino-1-(2-hydroxyethyl)-1H-pyrazol-2-ium-2-yl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate hydrochloride→S-(benzo[d]thiazol-2-yl) (Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate→(6R,7R)-3-[[5-Amino-1-(2-hydroxyethyl)-1H-pyrazol-2-ium-2-yl]methyl]-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

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