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

HRID 913232ノート

反応式

HRID 913232 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 23053668Dimethylsulfoxide ethyl acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5362cd58179f4effa83789ce8ce6c3a4
出典データセット
uspto-grants-2011_09
特許番号
US08026273B2

反応ノート

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