Dicyclohexylcarbodiimide → 7beta-[2-(2-Carbobenzoxyamino-5-fluoro-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid diphenylmethyl ester

HRID 126898Notes

Reaction equation

HRID 126898 reaction equation
[C:1]([NH:11][C:12]1[S:13][C:14]([F:24])=[C:15]([C:17](=[N:21][O:22][CH3:23])[C:18]([OH:20])=O)[N:16]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[C:25]1([CH:31]([O:38][C:39]([C:41]2[N:46]3[C:47](=[O:50])[C@@H:48]([NH2:49])[C@H:45]3[S:44][CH2:43][CH:42]=2)=[O:40])[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[C:25]1([CH:31]([O:38][C:39]([C:41]2[N:46]3[C:47](=[O:50])[C@@H:48]([NH:49][C:18](=[O:20])[C:17]([C:15]4[N:16]=[C:12]([NH:11][C:1]([O:3][CH2:4][C:5]5[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=5)=[O:2])[S:13][C:14]=4[F:24])=[N:21][O:22][CH3:23])[C@H:45]3[S:44][CH2:43][CH:42]=2)=[O:40])[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 9842110diphenylmethyl (6R,7R)-7-Amino-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylateHCID 536872122-(2-Carbobenzoxyamino-5-fluoro-4-thiazolyl)-2-methoxyiminoacetic acid

Product 1

HCID 1317121007beta-[2-(2-Carbobenzoxyamino-5-fluoro-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid diphenylmethyl esterYield 70.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 2-(2-carbobenzoxyamino-5-fluoro-4-thiazolyl)-2-methoxyiminoacetic acid (207 mg) and 7β-amino-3-cephem-4-carboxylic acid diphenylmethyl ester (207 mg) in dichloromethane (20 ml) is added dicyclohexylcarbodiimide (142 mg), and the mixture is stirred at 23° C. for 60 minutes and concentrated to remove dichloromethane. The residue is dissolved in ethyl acetate, filtered to remove solid material, and concentrated under reduced pressure. The resultant product is purified by silica gel column chromatography to afford 7β-[2-(2-carbobenzoxyamino-5-fluoro-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid diphenylmethyl ester (281 mg).

Workup

  1. concentrationconcentrated
  2. customto remove dichloromethane
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. filtrationfiltered
  5. customto remove solid material
  6. concentrationconcentrated under reduced pressure
  7. customThe resultant product is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fb222d2ffae54a0d86a32b6efac93ace
Source dataset
uspto-grants-1981_03
Patent number
US04254119

Reaction notes

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