Diisopropylethylamine → Diphenylmethyl 7beta-formamido-3-[(4-pyridyl)methylthio]-3-cephem-4-carboxylate

HRID 992679노트

반응식

HRID 992679 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].[SH:34][CH2:35][C:36]1[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=1.C(N(CC)C(C)C)(C)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:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:17])=[C:8]([S:34][CH2:35][C:36]3[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=3)[CH2:9][S:10][C@H:5]12)=[O:2]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 10863874Diphenylmethyl 7beta-formamido-3-methanesulfonyloxy-3-cephem-4-carboxylateHCID 13092602Pyridin-4-ylmethanethiol

생성물 1

HCID 88157711Diphenylmethyl 7beta-formamido-3-[(4-pyridyl)methylthio]-3-cephem-4-carboxylate수율 88.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of diphenylmethyl 7β-formamido-3-methanesulfonyloxy-3-cephem-4-carboxylate (14.66 g, 30 m mol) in DMF (103 ml) was added 4-(mercaptomethyl)pyridine (4.13 g, 33 m mol) at −20° C., followed by dropwise addition of N,N-diisopropylethylamine (3.88 g, 30 m mol). The mixture was stirred at the same temperature for 1.9 hours and poured into ice water (500 ml). The resulting precipitates were collected by filtration and washed with water. The powder was dissolved in THF, and ethyl acetate and water were added respective. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel to give diphenylmethyl 7β-formamido-3-[(4-pyridyl)methylthio]-3-cephem-4-carboxylate (13.73 g).

후처리

  1. customThe resulting precipitates
  2. filtrationwere collected by filtration
  3. washwashed with water
  4. dissolutionThe powder was dissolved in THF
  5. additionethyl acetate and water were added respective
  6. washThe separated organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customThe residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-cceead8440d241e1be5be0bda81c26b1
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06468995B1

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