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

HRID 992679ノート

反応式

HRID 992679 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-cceead8440d241e1be5be0bda81c26b1
出典データセット
uspto-grants-2002_10
特許番号
US06468995B1

反応ノート

読み込み中…