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

HRID 1166495

反応式

HRID 1166495 の反応式
[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

5

反応物 4

HCID 3776IsopropanolHCID 81531DiisopropylethylamineHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 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 CH2C12) gave 100 mg of a white solid which was used directly in the next reaction.

後処理

  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

出典と根拠

ORDレコード
ord-8c00c332793640df80adcda14a1054c4
出典データセット
uspto-grants-2003_09
特許番号
US06613743B2

関連ノート

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