Allyl chloroformate → tert-Butyl-[3-(2-chloro-pyrimidin-4-yl)-benzyl]-carbamic acid allyl ester

HRID 14908

반응식

HRID 14908 반응식
[C:1]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([Cl:19])[N:14]=2)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].Cl[C:21]([O:23][CH2:24][CH:25]=[CH2:26])=[O:22].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH2:24]([O:23][C:21](=[O:22])[N:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([Cl:19])[N:14]=2)[CH:8]=1)[CH:25]=[CH2:26]

참가 물질

5

반응물 3

HCID 18052Allyl chloroformateHCID 81531DiisopropylethylamineHCID 86603310tert-Butyl-[3-(2-chloro-pyrimidin-4-yl)-benzyl]-amine

생성물 1

HCID 86603311tert-Butyl-[3-(2-chloro-pyrimidin-4-yl)-benzyl]-carbamic acid allyl ester수율 61%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

tert-Butyl-[3-(2-chloro-pyrimidin-4-yl)-benzyl]-amine from the above reaction (1.33 g, 4.84 mmol) was treated with allyl chloroformate (0.77 mL) in methylene chloride (15 mL) with diisopropyl ethylamine (1.7 mL) at room temperature for 3 hours. The mixture was diluted with methylene chloride (50 mL), washed with water (2×), brine, dried over Na2SO4, filtered. Removal of the solvent followed by chromatography on silica gel (1:4 ethyl acetate:hexane eluent) afforded product in 61% yield. LC-MS showed the product had the expected M+H+ of 360. 1H NMR (Varian 300 MHz, CDCl3, shifts relative to the solvent peak at 7.24 ppm) 8.6 (d, 1H) 7.9 (d, 2H) 7.6 (d, 1H) 7.4 (m, 2H) 5.9 (m, 1H) 5.2 (m, 2H) 4.7 (s, 2H) 4.6 (d, 2H) 1.4 (s, 9H).

후처리

  1. washwashed with water (2×), brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customRemoval of the solvent
  5. customafforded product in 61% yield

출처 및 근거

ORD 기록
ord-ed400203ca504787827ba29c97dbf2c5
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732444B2

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