Pyridine → Benzhydryl (6R,7R)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 1905803Notes

Reaction equation

HRID 1905803 reaction equation
[C:1]1([CH:7]([O:14][C:15]([CH:17]2[N:22]3[C:23](=[O:26])[CH:24]([NH2:25])[C@H:21]3[S:20][CH2:19][CH:18]2OC(=O)C)=[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:37]1([CH2:43][C:44](Cl)=[O:45])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(N(CC)CC)C>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:44](=[O:45])[CH2:43][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[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

6

Reactant 4

HCID 1049PyridineHCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 704449447-Amino-3-acetoxycepham-4-carboxylic acid diphenylmethyl ester

Product 1

HCID 11237070Benzhydryl (6R,7R)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-amino-3-acetoxycepham-4-carboxylic acid diphenylmethyl ester (4) in dichloromethane (7 parts) cooling at -30° to -10° C. are added pyridine (1.7 equivalents) and phenylacetyl chloride (1.1 equivalents). After stirring for 30 minutes, the mixture is neutralized with triethylamine (1 to 9 equivalents), stirred at 0° to 5° C. for 24 hours, and diluted with ice water. The formed organic layer is taken, washed with hydrochloric acid and water, dried, and concentrated. The residue is crystallized from a mixture of ethyl acetate and ether to give 7beta-phenylacetylamino-3-cephem-4-carboxylic acid diphenylmethyl ester (6). Yield: 70.0%. mp. 170°-171° C. (decomposition).

Workup

  1. stirringstirred at 0° to 5° C. for 24 hours
  2. washwashed with hydrochloric acid and water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue is crystallized from a mixture of ethyl acetate and ether

Sources & evidence

ORD record
ord-cb187c1c08364e2580d48c6b7fad5d28
Source dataset
uspto-grants-1987_03
Patent number
US04647658

Reaction notes

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