Ammonia → 2-[1-(4-Bromo-phenyl)-1-carbamoyl-ethylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 71686

반응식

HRID 71686 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13](=[O:29])[NH:14][C:15]([C:22]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=1)([C:17](OCC)=[O:18])[CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH3:30]>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13](=[O:29])[NH:14][C:15]([C:22]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=1)([C:17](=[O:18])[NH2:30])[CH3:16])=[O:7])([CH3:3])([CH3:2])[CH3:4]

참가 물질

4

반응물 2

HCID 222AmmoniaHCID 666204492-[1-(4-Bromo-phenyl)-1-ethoxycarbonyl-ethylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 666205922-[1-(4-Bromo-phenyl)-1-carbamoyl-ethylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester수율 64%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a stirred solution of 2-[1-(4-bromo-phenyl)-1-ethoxycarbonyl-ethylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (280 mg, 0.6 mmol) in ethanol (8 mL) was bubbled through NH3 gas for 5 minutes at −78° C. The solution was stirred at ambient for 3 days in a sealed tube. Most of the volatile component was removed in vacuo, and the resulting residue was dissolved in ethyl acetate (150 mL), washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The obtained residue was purified by flash chromatography to provide the desired product as a colorless oil (169 mg, 64%). m/z 439.8, 441.8 (M+H)+.

후처리

  1. customMost of the volatile component was removed in vacuo
  2. dissolutionthe resulting residue was dissolved in ethyl acetate (150 mL)
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe obtained residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-aa708c828798479abc21e785676187ba
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822430B2

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