diphenylmethyl (6R,7R)-7-Amino-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate → 7beta-[2-Methoxyimino-2-(2-chloroacetamido-5-chloro-4-thiazolyl)acetamido]-3-cephem-4-carboxylic acid diphenylmethyl ester

HRID 126899Notes

Reaction equation

HRID 126899 reaction equation
[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:26])[C@@H:24]([NH2:25])[C@H:21]3[S:20][CH2:19][CH:18]=2)=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:27][CH2:28][C:29]([NH:31][C:32]1[S:33][C:34]([Cl:44])=[C:35]([C:37](=[N:41][O:42][CH3:43])[C:38](O)=[O:39])[N:36]=1)=[O:30]>ClCCl>[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:26])[C@@H:24]([NH:25][C:38](=[O:39])[C:37](=[N:41][O:42][CH3:43])[C:35]4[N:36]=[C:32]([NH:31][C:29](=[O:30])[CH2:28][Cl:27])[S:33][C:34]=4[Cl:44])[C@H:21]3[S:20][CH2:19][CH:18]=2)=[O:16])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 9842110diphenylmethyl (6R,7R)-7-Amino-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylateHCID 539831782-(2-Chloroacetamido-5-chloro-4-thiazolyl)-2-methoxyiminoacetic acid

Product 1

HCID 1317121017beta-[2-Methoxyimino-2-(2-chloroacetamido-5-chloro-4-thiazolyl)acetamido]-3-cephem-4-carboxylic acid diphenylmethyl esterYield 75.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7β-amino-3-cephem-4-carboxylic acid diphenylmethyl ester (1.10 g) in dichloromethane (120 ml) are added a solution of 2-(2-chloroacetamido-5-chloro-4-thiazolyl)-2-methoxyiminoacetic acid (1.20 g) and N,N-dicyclohexylcarbodiimide (0.80 g), and the mixture is stirred for 30 minutes at room temperature. After concentrating to remove dichloromethane, the obtained residue is treated with a small amount of ethyl acetate and filtered to remove insoluble material. The solution is concentrated in vacuo, and the residue is purified by chromatography on silica gel affording 7β-[2-methoxyimino-2-(2-chloroacetamido-5-chloro-4-thiazolyl)acetamido]-3-cephem-4-carboxylic acid diphenylmethyl ester (1.49 g). mp. 149°-151° C. when crystallized from benzene. Similarly prepared are compounds of Table 1.

Workup

  1. concentrationAfter concentrating
  2. customto remove dichloromethane
  3. additionthe obtained residue is treated with a small amount of ethyl acetate
  4. filtrationfiltered
  5. customto remove insoluble material
  6. concentrationThe solution is concentrated in vacuo
  7. customthe residue is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-cd179439e5bc45cbbb77b77e29c0cbc8
Source dataset
uspto-grants-1981_03
Patent number
US04254119

Reaction notes

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