Bromide ion → methyl (S)-3,3-dimethylbutan-2-yl(3-(4-fluorophenyl)-3-hydroxyhex-5-enyl)carbamate

HRID 2091512노트

반응식

HRID 2091512 반응식
[CH3:1][C:2]([CH3:22])([CH3:21])[C@@H:3]([N:5]([CH2:10][CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)=[O:13])[C:6](=[O:9])[O:7][CH3:8])[CH3:4].[Br-].[CH2:24]1[CH2:28]OC[CH2:25]1>>[CH3:22][C:2]([CH3:21])([CH3:1])[C@@H:3]([N:5]([CH2:10][CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)([OH:13])[CH2:28][CH:24]=[CH2:25])[C:6](=[O:9])[O:7][CH3:8])[CH3:4]

참가 물질

4

반응물 3

HCID 259Bromide ionHCID 8028TetrahydrofuranHCID 58485254(S)-methyl 3,3-dimethylbutan-2-yl(3-(4-fluorophenyl)-3-oxopropyl)carbamate

생성물 1

HCID 58485267methyl (S)-3,3-dimethylbutan-2-yl(3-(4-fluorophenyl)-3-hydroxyhex-5-enyl)carbamate수율 92%

실험 절차

To a solution of (S)-methyl 3,3-dimethylbutan-2-yl(3-(4-fluorophenyl)-3-oxopropyl)carbamate (4.5 g, 0.015 mol) in THF (60 mL) was added allymagnesium bromide (1 M, 30 mL, 0.03 mol) dropwise at −78° C. under N2. After adding completely, the reaction mixture was stirred at rt overnight. The reaction was quenched with saturated aqueous NH4Cl solution, and the mixture was extracted with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to give methyl (S)-3,3-dimethylbutan-2-yl(3-(4-fluorophenyl)-3-hydroxyhex-5-enyl)carbamate (4.80 g, 92%), which was used for the next step without further purification.

후처리

  1. additionAfter adding completely
  2. customThe reaction was quenched with saturated aqueous NH4Cl solution
  3. extractionthe mixture was extracted with EtOAc
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a3bd46523c3247459ff69ddd72a83521
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08440658B2

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