4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]- (2S,5R,6R)-, 1-(methoxycarbonyl)-2-oxopropyl 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)-, 1-(methoxycarbonyl)-2-oxopropyl ester, 4-oxide
• CAS No.: 59176-12-4
• Molecular Formula: C₂₁H₂₄N₂O₈S
• Molecular Weight: 464.496
• Mol file: 59176-12-4.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)-, 1-(methoxycarbonyl)-2-oxopropyl 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)-, 1-(methoxycarbonyl)-2-oxopropyl ester, 4-oxide

There total 1 articles about 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]- (2S,5R,6R)-, 1-(methoxycarbonyl)-2-oxopropyl 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:

→ 1ξ-oxo-6β-(2-phenyl-acetylamino)-1λ4-penicillanic acid (Ξ)-1-methoxycarbonyl-2-oxo-propyl ester (59176-12-4)

Guidance literature:

K-Salz des 6-Phenylacetamid-penicillansaeure-oxids, α-Chlor-acetessigsaeure-methylester;

Reference yield:

1ξ-oxo-6β-(2-phenyl-acetylamino)-1λ4-penicillanic acid (Ξ)-1-methoxycarbonyl-2-oxo-propyl ester (59176-12-4) → (6R)-3-methyl-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (Ξ)-1-methoxycarbonyl-2-oxo-propyl ester (59176-13-5)

Guidance literature:

With pyridinium dichloromethanephosphate; In 1,4-dioxane;

DOI:10.1246/cl.1977.1317

Reference yield:

1ξ-oxo-6β-(2-phenyl-acetylamino)-1λ4-penicillanic acid (Ξ)-1-methoxycarbonyl-2-oxo-propyl ester (59176-12-4) → (6R,7R)-7-[(2R)-2-{[(tert-butoxy)carbonyl]amino}-2-phenylacetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (28180-92-9)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridinium dichloromethanephosphate / dioxane

2: (i) PCl₅, CH₂Cl₂, (ii) /BRN= 5390956/

3: aq. NaNO₂ / acetone; acetic acid

With pyridinium dichloromethanephosphate; sodium nitrite; In 1,4-dioxane; acetic acid; acetone;

DOI:10.1246/cl.1977.1317

Downstream raw materials:

(6R)-3-methyl-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (Ξ)-1-methoxycarbonyl-2-oxo-propyl ester

(6R,7R)-7-[(2R)-2-{[(tert-butoxy)carbonyl]amino}-2-phenylacetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

(6R)-7t-((R)-2-tert-butoxycarbonylamino-2-phenyl-acetylamino)-3-methyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (Ξ)-1-methoxycarbonyl-2-oxo-propyl ester