(2S,3'Z)-Cefprozil

Base Information

• Chemical Name: (2S,3'Z)-Cefprozil
• CAS No.: 110764-35-7
• Molecular Formula: C18H19N3O5S
• Molecular Weight: 389.42556
• Hs Code.: 2941906000
• Mol file: 110764-35-7.mol

Synonyms:(2S,3'Z)-Cefprozil;(6R,7R)-7-[(S)-2-Amino-2-(4-hydroxyphenyl)acetamido]-8-oxo-3-[(Z)-prop-1-enyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;Cefprozil L-Epimer;Cefprozil L-Epimer (30 mg) ((6R,7R)-7-[(S)-2-amino-2-(4-hydroxyphenyl)acetamido]-8-oxo-3-[(Z)-prop-1-enyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid)

Chemical Property of (2S,3'Z)-Cefprozil

Chemical Property:

• Boiling Point: 803.1±65.0 °C(Predicted)
• PKA: 2.92±0.50(Predicted)
• PSA: 158.26000
• Density: 1.53±0.1 g/cm3(Predicted)
• LogP: 1.73580

Purity/Quality:

98% ^*data from raw suppliers

(2S,3’Z)-Cefprozil ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: L-Epimer of Cefprozil (C243910), an semisynthetic oral cephalosporin consisting of approx. 90:10 Z/E isomeric mixture and is an antibacterial agent.

Technology Process of (2S,3'Z)-Cefprozil

There total 2 articles about (2S,3'Z)-Cefprozil 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:

cis-7-amino-3-propen-1-yl-3-cephem-4-carboxylic acid (106447-44-3) + trans-7-amino-3-propen-1-yl-3-cephem-4-carboxylic acid (107937-01-9) + potassium (D)-N-[1-methoxycarbonylpropen-2-yl]-α-amino-p-hydroxyphenylacetate (337307-47-8) → 7-[D-α-amino-α-(4-hydroxyphenyl)acetamido]-3-(1-propen-1-yl)-3-cephem-4-carboxylic acid (110764-35-7) + (6R,7R)-7-[(2R)-2-amino-2-(4-hydroxylphenyl)acetamido]-3-propenyl-3-cephem-4-carboxylic acid N,N-dimethylformamide solvate

Guidance literature:

cis-7-amino-3-propen-1-yl-3-cephem-4-carboxylic acid; trans-7-amino-3-propen-1-yl-3-cephem-4-carboxylic acid; With 1H-imidazole; chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane; for 3.5 - 4h; Heating / reflux;

potassium (D)-N-[1-methoxycarbonylpropen-2-yl]-α-amino-p-hydroxyphenylacetate; With 4-methyl-morpholine; chloroformic acid ethyl ester; In DMF (N,N-dimethyl-formamide); dichloromethane; at -45 - -20 ℃; for 3 - 4h;

With hydrogenchloride; ammonia; pyrographite; more than 3 stages;

Reference yield:

C26H33N3O7SSi → 7-[D-α-amino-α-(4-hydroxyphenyl)acetamido]-3-(1-propen-1-yl)-3-cephem-4-carboxylic acid (110764-35-7)

Guidance literature:

With hydrogenchloride; water; In dichloromethane; at -40 - 10 ℃; for 0.5h; pH=0.5; Product distribution / selectivity;

upstream raw materials:

cis-7-amino-3-propen-1-yl-3-cephem-4-carboxylic acid

trans-7-amino-3-propen-1-yl-3-cephem-4-carboxylic acid

potassium (D)-N-[1-methoxycarbonylpropen-2-yl]-α-amino-p-hydroxyphenylacetate

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF (Z)-ISOMER ENRICHED 7-AMINO-3-PROPEN-1-YL-3-CEPHEM-4- CARBOXYLIC ACID". Page 13-14. . Retrieved 2010/02/06.