Ertapenem Oxazinone Impurity

Base Information

• Chemical Name: Ertapenem Oxazinone Impurity
• CAS No.: 866186-68-7
• Molecular Formula: C₂₃H₂₅N₃O₉S
• Molecular Weight: 519.532
• UNII: 339FE3NYB7
• Mol file: 866186-68-7.mol

Synonyms:866186-68-7;(3S,4S,4aS,5R)-6-[[(3S,5S)-5-[[(3-Carboxyphenyl)amino]carbonyl]-3-pyrrolidinyl]thio]-3,4,4a,5-tetrahydro-3,5-dimethyl-1-oxo-1H-pyrrolo[1,2-c][1,3]oxazine-4,7-dicarboxylic Acid;Ertapenem Oxazinone Impurity;339FE3NYB7;(3S,4S,4aS,5R)-6-(((3S,5S)-5-((3-Carboxyphenyl)carbamoyl)pyrrolidin-3-yl)thio)-3,5-dimethyl-1-oxo-3,4,4a,5-tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazine-4,7-dicarboxylic acid;(4aS,5R)-6-[[(3S,5S)-5-[[(3-Carboxyphenyl)amino]carbonyl]-3-pyrrolidinyl]thio]-3,4,4a,5-tetrahydro-3,5-dimethyl-1-oxo-1H-pyrrolo[1,2-c][1,3]oxazine-4,7-dicarboxylic acid;1H-Pyrrolo[1,2-c][1,3]oxazine-4,7-dicarboxylic acid, 6-[[(3S,5S)-5-[[(3-carboxyphenyl)amino]carbonyl]-3-pyrrolidinyl]thio]-3,4,4a,5-tetrahydro-3,5-dimethyl-1-oxo-, (3S,4S,4aS,5R)-;1H-Pyrrolo[1,2-c][1,3]oxazine-4,7-dicarboxylic acid, 6-[[(3S,5S)-5-[[(3-carboxyphenyl)amino]carbonyl]-3-pyrrolidinyl]thio]-3,4,4a,5-tetrahydro-3,5-dimethyl-1-oxo-, (4aS,5R)-

Chemical Property of Ertapenem Oxazinone Impurity

Chemical Property:

• PSA: 211.36000
• LogP: 2.55920
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 7
• Exact Mass: 519.13115056
• Heavy Atom Count: 36
• Complexity: 1000

Purity/Quality:

≧95%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2C(C(OC(=O)N2C(=C1SC3CC(NC3)C(=O)NC4=CC=CC(=C4)C(=O)O)C(=O)O)C)C(=O)O
• Isomeric SMILES: C[C@@H]1[C@@H]2[C@@H]([C@@H](OC(=O)N2C(=C1S[C@H]3C[C@H](NC3)C(=O)NC4=CC=CC(=C4)C(=O)O)C(=O)O)C)C(=O)O

Technology Process of Ertapenem Oxazinone Impurity

There total 7 articles about Ertapenem Oxazinone Impurity 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:

carbon dioxide (124-38-9,18923-20-1) + [4R-[3(3S,5S)-4α,5β,6β(R)]]-3-[[5-[[(3-carboxyphenyl)amino]carbonyl]-3-pyrrolidinyl]thio]-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0.]hept-2-ene-2-carboxylic acid monosodium → 6-[5-(3-carboxy-phenylcarbamoyl)-pyrrolidin-3-ylsulfanyl]-3,5-dimethyl-1-oxo-3,4,4a,5-tetrahydro-pyrrolo[1,2-c][1,3]oxazine-4,7-dicarboxylic acid (866186-68-7)

Guidance literature:

With sodium hydrogencarbonate; In water; at 20 ℃; for 24h; under 31028.9 Torr;

DOI:10.1021/jo0501442

Reference yield:

(4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (93711-81-0,90776-59-3,189188-38-3) → 6-[5-(3-carboxy-phenylcarbamoyl)-pyrrolidin-3-ylsulfanyl]-3,5-dimethyl-1-oxo-3,4,4a,5-tetrahydro-pyrrolo[1,2-c][1,3]oxazine-4,7-dicarboxylic acid (866186-68-7)

Guidance literature:

Multi-step reaction with 3 steps

1: diisopropylamine / dimethylformamide / -30 °C

2: NaOH / Pd/C / ethyl acetate; H₂O / pH 7.1 - 7.2

3: NaHCO₃ / H₂O / 24 h / 20 °C / 31028.9 Torr

With sodium hydroxide; sodium hydrogencarbonate; diisopropylamine; palladium on activated charcoal; In water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo0501442

Reference yield:

C12H12N2O3S(2-)*2Na(1+) → 6-[5-(3-carboxy-phenylcarbamoyl)-pyrrolidin-3-ylsulfanyl]-3,5-dimethyl-1-oxo-3,4,4a,5-tetrahydro-pyrrolo[1,2-c][1,3]oxazine-4,7-dicarboxylic acid (866186-68-7)

Guidance literature:

Multi-step reaction with 3 steps

1: N-ethylpyrrolidinone; sodium hydroxide; isopropyl acetate / H₂O / -45 - -40 °C / cooling

2: NaHCO₃; N-ethylpyrrolidinone / Pd/C / H₂O / pH 7 - 8

3: NaHCO₃ / H₂O / 24 h / 20 °C / 31028.9 Torr

With 1-ethyl-2-pyrrolidinone; sodium hydroxide; Isopropyl acetate; sodium hydrogencarbonate; palladium on activated charcoal; In water;

DOI:10.1021/jo0501442

upstream raw materials:

carbon dioxide

(2S,4S)-2-[[(3-carboxyphenyl)amino]carbonyl]-4-mercapto-1-(4-nitrobenzyl)pyrrolidine carboxylate

(4-nitrophenyl)methyl (4R,5S,6S)-3-[[(3S,5S)-5-[[(-carboxyphenyl)amino]carbonyl]-1-[[(4-nitrophenyl)methyoxy]carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

(4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate