Dichloromethane → Diphenylmethyl 7-(2-thienylacetamido)-3-(1-acetoxyethyl)-3-cephem-4-carboxylate

HRID 372871Notes

Reaction equation

HRID 372871 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:26](=[O:27])[N:12]2[C:13]([C:23]([OH:25])=[O:24])=[C:14]([CH:17]([O:19][C:20](=[O:22])[CH3:21])[CH3:18])[CH2:15][S:16][C@H:11]12)=[O:8].C(Cl)Cl.[C:31]1([C:37]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[N+]=[N-])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CO.CCOCC>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:26](=[O:27])[N:12]2[C:13]([C:23]([O:25][CH:37]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[O:24])=[C:14]([CH:17]([O:19][C:20](=[O:22])[CH3:21])[CH3:18])[CH2:15][S:16][C@H:11]12)=[O:8]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 612301,1'-(Diazomethylene)bis(benzene)HCID 706176497-(2-Thienylacetamido)-3-(1-acetoxyethyl)-3-cephem-4-carboxylic acid

Product 1

HCID 70617769Diphenylmethyl 7-(2-thienylacetamido)-3-(1-acetoxyethyl)-3-cephem-4-carboxylateYield 70%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 7-(2-thienylacetamido)-3-(1-acetoxyethyl)-3-cephem-4-carboxylic acid (stereoisomer A: 88 mg) in mixture (5 ml) of methanol and methylene chloride (1:1) is added a solution of diphenyldiazomethane in ether until the red color of the solution does no more disappear at 55° C on standing. After 3 hours, the reaction mixture is concentrated to give the residue which is stirred in a mixture of ether and petroleum ether. The supernatant is removed, and resulting precipitate is recrystallized from petroleum ether to give diphenylmethyl 7-(2-thienylacetamido)-3-(1-acetoxyethyl)-3-cephem-4-carboxylate (stereoisomer A: 85 mg). m.p. 161-163° C. Yield: 70%.

Workup

  1. customno more disappear at 55° C
  2. concentrationthe reaction mixture is concentrated
  3. customto give the residue which
  4. customThe supernatant is removed
  5. customresulting precipitate
  6. customis recrystallized from petroleum ether

Sources & evidence

ORD record
ord-b207f072fff7422d91881db5033fc4e6
Source dataset
uspto-grants-1978_05
Patent number
US04092474

Reaction notes

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