Acetic Anhydride → (S)-4-tert-butoxycarbonylamino-4-[4-(N-acetylhydroxycarbamimidoyl)-benzyl carbamoyl]-butyric acid benzyl ester

HRID 576550ノート

反応式

HRID 576550 の反応式
[CH2:1]([O:8][C:9](=[O:35])[CH2:10][CH2:11][C@H:12]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:13](=[O:26])[NH:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[NH:25])[NH:23][OH:24])=[CH:18][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:36](OC(=O)C)(=[O:38])[CH3:37]>C(O)(=O)C>[CH2:1]([O:8][C:9](=[O:35])[CH2:10][CH2:11][C@H:12]([NH:27][C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])[C:13](=[O:26])[NH:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[NH:25])[N:23]([OH:24])[C:36](=[O:38])[CH3:37])=[CH:18][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 7918Acetic AnhydrideHCID 178454209(S)-4-tert-butoxycarbonylamino-4-[4-(N-hydroxycarbamimidoyl)-benzyl carbamoyl]-butyric acid benzyl ester

生成物 1

HCID 86658625(S)-4-tert-butoxycarbonylamino-4-[4-(N-acetylhydroxycarbamimidoyl)-benzyl carbamoyl]-butyric acid benzyl ester収率 91%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A solution of compound R (14.8 g, 20.0 mmol) and acetic anhydride (5.7 ml, 60.0 mmol) in acetic acid (100 ml) was stirred at room temperature for 45 min, and then solvent was evaporated in vacuo. The resultant residue was dissolved in EtOAc (300 ml) and extracted with water (2×75 ml) and brine (75 ml). The organic layer was then dried over MgSO4, evaporated and dried in vacuo to provide compound S (9.58 g, 18.2 mmol) as yellowish solid. LC-MS [M+H] 527.6 (C27H34N4O7+H, calc: 527.9). Compound S was used without further purification.

後処理

  1. customsolvent was evaporated in vacuo
  2. dissolutionThe resultant residue was dissolved in EtOAc (300 ml)
  3. extractionextracted with water (2×75 ml) and brine (75 ml)
  4. dry with materialThe organic layer was then dried over MgSO4
  5. customevaporated
  6. customdried in vacuo

出典と根拠

ORDレコード
ord-fdf19fcdf17f4d1fa20b9934b5b92232
出典データセット
uspto-grants-2015_05
特許番号
US09040032B2

反応ノート

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