Pyridine → 3-Acetoxy-7beta-phenylacetylaminocepham-4-carboxylic acid diphenylmethyl ester

HRID 1905798Notes

Reaction equation

HRID 1905798 reaction equation
[C:1]1([CH:7]([O:14][C:15]([CH:17]2[N:22]3[C:23](=[O:35])[C@@H:24]([NH:25][C:26](=[O:34])[CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C@H:21]3[S:20][CH2:19][CH:18]2[OH:36])=[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.N1C=CC=CC=1.[C:43](OC(=O)C)(=[O:45])[CH3:44]>ClCCl>[C:1]1([CH:7]([O:14][C:15]([CH:17]2[N:22]3[C:23](=[O:35])[C@@H:24]([NH:25][C:26](=[O:34])[CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C@H:21]3[S:20][CH2:19][CH:18]2[O:36][C:43](=[O:45])[CH3:44])=[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

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 1364457351762-51-7

Product 1

HCID 137854823-Acetoxy-7beta-phenylacetylaminocepham-4-carboxylic acid diphenylmethyl esterYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-hydroxy-7beta-phenylacetylaminocepham-4-carboxylic acid diphenylmethyl ester (2) in dichloromethane (13 parts) at 0° C. are added pyridine (6 equivalents) and acetic anhydride (6 equivalents). After 14 hours at 0° to 5° C., the mixture is diluted with ice-water. The organic layer is taken, washed with hydrochloric acid, aqueous sodium hydrogen carbonate, and water, dried, and concentrated. The reaction is crystallized from a mixture of dichloromethane and hexane to give 3-acetoxy-7beta-phenylacetylaminocepham-4-carboxylic acid diphenylmethyl ester (3a). Yield: 98.1%. mp. 187°-188° C. (decomposition).

Workup

  1. washwashed with hydrochloric acid, aqueous sodium hydrogen carbonate, and water
  2. customdried
  3. concentrationconcentrated
  4. customThe reaction is crystallized from a mixture of dichloromethane and hexane

Sources & evidence

ORD record
ord-45fcdf730507463e8a10c6e6af8f823c
Source dataset
uspto-grants-1987_03
Patent number
US04647658

Reaction notes

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