Triethylamine → N-methoxyethoxyacetyl-(L)-valine tert-butyl ester

HRID 1291776

반응식

HRID 1291776 반응식
C(N(CC)CC)C.[C:8]([O:12][C:13](=[O:19])[C@H:14]([CH:16]([CH3:18])[CH3:17])[NH2:15])([CH3:11])([CH3:10])[CH3:9].[CH3:20][O:21][CH2:22][CH2:23][O:24][CH2:25][C:26](O)=[O:27].C(OP(C#N)(=O)OCC)C>CN(C=O)C.C(Cl)Cl>[C:8]([O:12][C:13](=[O:19])[C@H:14]([CH:16]([CH3:17])[CH3:18])[NH:15][C:26](=[O:27])[CH2:25][O:24][CH2:23][CH2:22][O:21][CH3:20])([CH3:11])([CH3:10])[CH3:9]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 27642(2-Methoxyethoxy)acetic acidHCID 76257Diethyl cyanophosphonateHCID 114626tert-Butyl L-valinate

생성물 1

HCID 80707032N-methoxyethoxyacetyl-(L)-valine tert-butyl ester수율 81.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

At 0°, 6.4 ml (45.7 mmol) of triethylamine are added to a solution of 5 g (23.9 mmol) of (L)-valine tert-butyl ester, 2.91 g (21.7 mmol) of 2-(methoxyethoxy)-acetic acid and 3.55 g (21.7 mmol) of cyanophosphonic acid diethyl ester in 30 ml of DMF and the mixture is then stirred overnight at RT. The reaction mixture is diluted with methylene chloride, washed in succession with 10% citric acid, saturated sodium hydrogen carbonate solution and saturated sodium chloride solution and, after concentration by evaporation of the organic phase, yields 5.1 g of N-methoxyethoxyacetyl-(L)-valine tert-butyl ester, which is stirred for 1 h at RT in 22 ml of a (1:1) mixture of methylene chloride and TFA. Concentration by evaporation of the reaction solution yields the title compound in the form of a colourless oil. 1H-NMR (200 MHz, CDCl3): 10.0 (s, broad, 1H), 7.62 d, broad, 1H), 4.55 (m, 1H), 4.10 (s, 2H), 3.70 (m, 2H), 3.58 (m, 2H), 3.40 (s, 3H), 2.28 (m, 1H), 0.98 (d, J=7 Hz, 3H), 0.95 (d, J=7 Hz, 3H).

후처리

  1. washwashed in succession with 10% citric acid, saturated sodium hydrogen carbonate solution and saturated sodium chloride solution
  2. concentrationafter concentration
  3. customby evaporation of the organic phase

출처 및 근거

ORD 기록
ord-6319baa8aaeb4eb9aab4cda2aff0c823
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05753652

연결된 노트

불러오는 중…