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

HRID 576550노트

반응식

HRID 576550 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fdf19fcdf17f4d1fa20b9934b5b92232
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040032B2

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