Isopropanol → tert-Butyl-N-((1S,2R)-1-benzyl-3-(tert-butyloxy)amino-2-hydroxypropyl)carbamate

HRID 29189

반응식

HRID 29189 반응식
[O:1]1[CH2:3][C@@H:2]1[C@@H:4]([NH:12][C:13](=[O:15])[O-:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl.[C:17]([O:21][NH2:22])([CH3:20])([CH3:19])[CH3:18].C(N([CH:29]([CH3:31])[CH3:30])CC)(C)C.[CH:32](O)(C)C>>[C:29]([O:14][C:13](=[O:15])[NH:12][C@@H:4]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C@H:2]([OH:1])[CH2:3][NH:22][O:21][C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:31])([CH3:32])[CH3:30]

참가 물질

5

반응물 4

HCID 3776IsopropanolHCID 81531DiisopropylethylamineHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 20638362(1S)-1-[(2S)oxiranyl]-2-phenylethylcarbamate

생성물 1

HCID 59090702tert-Butyl-N-((1S,2R)-1-benzyl-3-(tert-butyloxy)amino-2-hydroxypropyl)carbamate

실험 절차

tert-Butyl-N-((1S)-1-[(2S)oxiranyl]-2-phenylethylcarbamate (0.155 g, 0.59 mmol) and O-(tert-butyl)hydroxylamine hydrochloride (0.089 g, 0.71 mmol) were heated with diisopropylethylamine (0.154 ml, 0.88 mmol) in isopropanol (2 ml) in a sealed tube at 60° C. for 5 days. The reaction mixture was concentrated in vacuo, taken up in EtOAc, washed with sat. aq. NaHCO3, and brine. The organic phase was dried over MgSO4, filtered and solvent removed in vacuo. Purication by column chromatography (1% MeOH in CH2Cl2) gave 100 mg of a white solid which was used directly in the next reaction.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washwashed with sat. aq. NaHCO3, and brine
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. customsolvent removed in vacuo

출처 및 근거

ORD 기록
ord-52b8f8f029684768afcaa2b5b52f915e
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419967B2

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