Triethylamine → Benzhydryl 7-amino-3-cephem-4-carboxylate

HRID 1905802Notes

Reaction equation

HRID 1905802 reaction equation
[C:1]1([CH:7]([O:14][C:15]([CH:17]2[N:22]3[C:23](=[O:26])[C@@H: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.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])[CH:24]([NH2:25])[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 8471TriethylamineHCID 137854883-Acetoxy-7beta-aminocepham-4-carboxylic acid diphenylmethyl ester

Product 1

HCID 12098365Benzhydryl 7-amino-3-cephem-4-carboxylateYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-acetoxy-7beta-aminocepham-4-carboxylic acid diphenylmethyl ester (4a) in dichloromethane cooling at -25° to -20° C. is added triethylamine (1 to 3 equivalents). The mixture is warmed slowly up to 0° to 5° C. and let stand overnight. To this is added ice-water (20 parts), stirred for 20 minutes, and extracted with dichloromethane. The extract is washed with hydrochloric acid, water, aqueous 7% sodium hydrogen carbonate, and aqueous 5% sodium chloride, dried, and concentrated. The residue is crystallized from ethyl acetate to give 7beta-amino-3-cephem-4-carboxylic acid diphenylmethyl ester (5). Yield 61.0% from (1). mp. 159°-160° C. (decomposition).

Workup

  1. temperatureThe mixture is warmed slowly up to 0° to 5° C.
  2. extractionextracted with dichloromethane
  3. washThe extract is washed with hydrochloric acid, water, aqueous 7% sodium hydrogen carbonate, and aqueous 5% sodium chloride
  4. customdried
  5. concentrationconcentrated
  6. customThe residue is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-9a013a5805d84b7aac45f42fa7fa92b0
Source dataset
uspto-grants-1987_03
Patent number
US04647658

Reaction notes

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