Triethylamine → (S)-N-CBZ-valinol

HRID 326536노트

반응식

HRID 326536 반응식
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

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 640993L-Valinol

생성물 1

HCID 10900657(S)-N-CBZ-valinol수율 79.5%

시약·촉매·용매 1

HCID 6212Chloroform용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-3f551c17853f43e9992170149f9e5f33
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05270301

반응 노트

불러오는 중…