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

Reaktionsgleichung

[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]

Komponenten

Edukt 4

HCID 3776Isopropanol

HCID 81531Diisopropylethylamine

HCID 2777906O-tert-butylhydroxylamine hydrochloride

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

Produkt 1

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

Versuchsvorschrift

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.