Triethylamine → 2-((S)-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)ethyl methanesulfonate

HRID 2091518노트

반응식

HRID 2091518 반응식
[CH3:1][C:2]([CH3:23])([CH3:22])[C@@H:3]([N:5]1[CH2:10][CH2:9][C@@:8]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)([CH2:11][CH2:12][OH:13])[O:7][C:6]1=[O:21])[CH3:4].C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>C(Cl)Cl>[CH3:31][S:32]([O:13][CH2:12][CH2:11][C@@:8]1([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[O:7][C:6](=[O:21])[N:5]([C@H:3]([C:2]([CH3:22])([CH3:1])[CH3:23])[CH3:4])[CH2:10][CH2:9]1)(=[O:34])=[O:33]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58485265(S)-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-6-(2-hydroxyethyl)-1,3-oxazinan-2-one

생성물 1

HCID 866587272-((S)-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)ethyl methanesulfonate수율 102.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (S)-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-6-(2-hydroxyethyl)-1,3-oxazinan-2-one (220 mg, 0.68 mmol) and triethylamine (206 mg, 2.04 mmol) in CH2Cl2 (5 mL) was added methanesulfonyl chloride (233 mg, 2.04 mmol) at 0° C., and the reaction mixture was stirred at rt till the reaction was over. The reaction was quenched with H2O. The mixture was extracted with EtOAc, and the organic phase was washed with brine, dried over Na2SO4, filtered and concentrated to give crude 2-((S)-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)ethyl methanesulfonate (280 mg, crude), which was used for the next step without further purification.

후처리

  1. customThe reaction was quenched with H2O
  2. extractionThe mixture was extracted with EtOAc
  3. washthe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e8b3680c555943c6bcae64bac2ef68d9
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08440658B2

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