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

反応式

[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]

参加物

反応物 4

HCID 3776Isopropanol

HCID 81531Diisopropylethylamine

HCID 2777906O-tert-butylhydroxylamine hydrochloride

HCID 20638362(1S)-1-[(2S)oxiranyl]-2-phenylethylcarbamate

生成物 1

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

実験手順

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.