Triethylamine → (S)-N-CBZ-valinol

HRID 326536

反応式

HRID 326536 の反応式
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:12][C@H:13]([CH2:17][OH:18])[CH:14]([CH3:16])[CH3:15].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:5]([O:4][C:2]([NH:12][C@H:13]([CH2:17][OH:18])[CH:14]([CH3:16])[CH3:15])=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 640993L-Valinol

生成物 1

HCID 10900657(S)-N-CBZ-valinol収率 79.5%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
0 °C

実験手順

Benzyl chloroformate (91.0 g, 95% purity) was added dropwise over a period of 1 h to a precooled (0° C.) solution of L-valinol (50.0 g) and triethylamine (60.0 g) in chloroform (1500 ml). The reaction mixture was stirred for 1 h at 0° C. and then allowed to warm to,room temperature over 2 h. After the reaction mixture was evaporated, ethyl acetate (1500 ml) was added to the residue and the organic solution was washed (1N NaOH, brine), dried (MgSO4), and evaporated. The residue was purified by flash chromatography, using a stepwise gradient elution of ether:hexane (1:5) followed by ether, to give the alcohol (91.4 g) as a white waxy solid; TLC, Rf =0.23, hexane:ethanol (50:50).

後処理

  1. temperatureto warm to,room temperature over 2 h
  2. customAfter the reaction mixture was evaporated
  3. additionethyl acetate (1500 ml) was added to the residue
  4. washthe organic solution was washed (1N NaOH, brine)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by flash chromatography
  8. washa stepwise gradient elution of ether:hexane (1:5)

出典と根拠

ORDレコード
ord-3f551c17853f43e9992170149f9e5f33
出典データセット
uspto-grants-1993_12
特許番号
US05270301

関連ノート

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