4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]- (2S,5R,6R)-, methyl ester, 4-oxide

Base Information

• Chemical Name: 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]- (2S,5R,6R)-, methyl ester, 4-oxide
• CAS No.: 40578-79-8
• Molecular Formula: C17H20N2O5S
• Molecular Weight: 364.422
• Mol file: 40578-79-8.mol

Synonyms:

Chemical Property of 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]- (2S,5R,6R)-, methyl ester, 4-oxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]- (2S,5R,6R)-, methyl ester, 4-oxide

There total 7 articles about 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]- (2S,5R,6R)-, methyl ester, 4-oxide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

methanol (67-56-1) + Penicillin G 1-(s)-oxide (4052-54-4) → 1ξ-oxo-6β-(2-phenyl-acetylamino)-1λ4-penicillanic acid methyl ester (40578-79-8)

Guidance literature:

With dmap; methanesulfonic acid; triethylamine; 1.) THF, 1 h, 2.) -10 deg C, 1 h;

Reference yield: 60.0%

6β-(diphenylacetyl)aminopenicillanate 1R-sulfoxide (101760-75-2) → methyl 6β-(phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2α-carboxylate 1α-S-oxide (24652-72-0,24652-73-1,35345-03-0,40578-79-8,41536-91-8,59751-74-5,59751-75-6)

Guidance literature:

With ammonium acetate; zinc; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1021/jo00360a030

Reference yield:

penicillin G methyl ester (653-89-4) → methyl 6β-(phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2α-carboxylate 1α-S-oxide (24652-72-0,24652-73-1,35345-03-0,40578-79-8,41536-91-8,59751-74-5,59751-75-6)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine, PCl₅ / benzene / 1 h / 0 °C

2: toluene / 1.5 h / 55 - 60 °C

3: 67 percent / m-chloroperbenzoic acid (MCPBA) / benzene / 0.5 h / Ambient temperature

4: 60 percent / Zn, 1 M aq. AcONH₄ / tetrahydrofuran / 2 h / Ambient temperature

With pyridine; phosphorus pentachloride; ammonium acetate; 3-chloro-benzenecarboperoxoic acid; zinc; In tetrahydrofuran; toluene; benzene;

DOI:10.1021/jo00360a030

upstream raw materials:

penicillin G methyl ester

methanol

Penicillin G 1-(s)-oxide

6β-(diphenylacetyl)aminopenicillanate 1R-sulfoxide

Downstream raw materials:

2-{(2R,3R)-2-[(2R,3S)-1-(1-Methoxycarbonyl-2-methyl-propenyl)-4-oxo-3-phenylacetylamino-azetidin-2-yldisulfanyl]-4-oxo-3-phenylacetylamino-azetidin-1-yl}-3-methyl-but-2-enoic acid methyl ester

bis<(3S,4R)-3-methoxy-1-(1-methoxycarbonyl-2-methylprop-1-enyl)-2-oxo-3-phenylacetamidoazetidin-4-yl> disulfide

(3S,4R)-3-methoxy-1-(1-methoxycarbonyl-2-methylprop-1-enyl)-4-methylthio-3-phenylacetamido-2-azetidinone

2-((1S,5R)-3-Benzyl-1-methoxy-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-methyl-but-2-enoic acid methyl ester