Ethyl Acetate → Diphenylmethyl 7beta-formamido-3-[(1,2,3-thiadiazol-5-yl)thio]-3-cephem-4-carboxylate

HRID 992687노트

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HRID 992687 반응식
[CH:1]([NH:3][C@@H:4]1[C:32](=[O:33])[N:6]2[C:7]([C:16]([O:18][CH:19]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])=[C:8](OS(C)(=O)=O)[CH2:9][S:10][C@H:5]12)=[O:2].[Na].[SH:35][C:36]1[S:40][N:39]=[N:38][CH:37]=1.C(OCC)(=O)C>CN(C=O)C>[CH:1]([NH:3][C@@H:4]1[C:32](=[O:33])[N:6]2[C:7]([C:16]([O:18][CH:19]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[O:17])=[C:8]([S:35][C:36]3[S:40][N:39]=[N:38][CH:37]=3)[CH2:9][S:10][C@H:5]12)=[O:2]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 5360545SodiumHCID 10863874Diphenylmethyl 7beta-formamido-3-methanesulfonyloxy-3-cephem-4-carboxylateHCID 178527744HCID 178527744, 화합물

생성물 1

HCID 88157740Diphenylmethyl 7beta-formamido-3-[(1,2,3-thiadiazol-5-yl)thio]-3-cephem-4-carboxylate수율 91.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
-20 °C

실험 절차

To a solution of diphenylmethyl 7β-formamido-3-methanesulfonyloxy-3-cephem-4-carboxylate (1 g) in DMF (10 ml) was added sodium salt of 5-mercapto-1,2,3-thiadiazole (445 mg) at −30° C. After being stirred at −20° C. for 1 hour, the mixture was poured into a mixture of ice water and ethyl acetate. The organic layer was separated washed with water and brine, dried over magnesium sulfate, and evaporated to give diphenylmethyl 7β-formamido-3-[(1,2,3-thiadiazol-5-yl)thio]-3-cephem-4-carboxylate (961 mg).

후처리

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

출처 및 근거

ORD 기록
ord-dc21ee5a53d540c6a6e01aa80d64226b
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06468995B1

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