Diisopropylethylamine → ethyl (4R)-4-(tert-butoxycarbonylamino)-4-formylbutanoate

HRID 913232노트

반응식

HRID 913232 반응식
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH2:6][C@@H:7]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8][OH:9])[CH3:2].C(N(C(C)C)CC)(C)C>CS(C)=O.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH2:6][C@H:7]([CH:8]=[O:9])[NH:10][C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])[CH3:2]

참가 물질

4

반응물 2

HCID 81531DiisopropylethylamineHCID 57351319Ethyl (4R)-4-[(tert-butoxycarbonyl)amino]-5-hydroxypentanoate

생성물 1

HCID 57894011ethyl (4R)-4-(tert-butoxycarbonylamino)-4-formylbutanoate수율 102.6%

시약·촉매·용매 1

HCID 23053668Dimethylsulfoxide ethyl acetate용매

실험 절차

Under an atmosphere of argon, to a mixed solution of (4R)-4-t-butoxycarbonylamino-5-hydroxypentanoic acid ethyl ester (1.62 g) and diisopropylethylamine (6.5 ml) in dimethylsulfoxide-ethyl acetate (1:1, 40 mL) was added sulfur trioxide pyridine complex (2.96 g) in ice bath and the mixture was stirred in ice bath for 1 hour. The reaction solution was poured into ice water and extracted with ethyl acetate. The organic layer was washed with 0.5N hydrochloric acid, water and brine, dried over anhydrous magnesium sulfate and concentrated to give the title compound (1.65 g) having the following physical data.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with 0.5N hydrochloric acid, water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-5362cd58179f4effa83789ce8ce6c3a4
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026273B2

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