p-Toluenesulfonic acid monohydrate → (S)-tert-butyl 1-hydroxybut-3-en-2-ylcarbamate

HRID 711999노트

반응식

HRID 711999 반응식
CC1(C)[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:5]([CH:14]=[CH2:15])[CH2:4][O:3]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.C([O-])(O)=O.[Na+]>[OH:3][CH2:4][C@@H:5]([NH:6][C:7](=[O:8])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH:14]=[CH2:15]

참가 물질

5

반응물 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 11020618tert-Butyl (4S)-4-ethenyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

생성물 1

HCID 11041481(S)-tert-butyl 1-hydroxybut-3-en-2-ylcarbamate수율 76%

시약·촉매·용매 2

HCID 887Methanol용매HCID 516892Sodium Bicarbonate용매

실험 절차

To a solution of tert-butyl (4S)-2,2-dimethyl-4-vinyl-1,3-oxazolidine-3-carboxylate (1.90 g, 8.36 mmol) in methanol (83 mL) was added p-toluenesulfonic acid monohydrate (0.80 g, 4.2 mmol) at 0° C. The mixture was slowly warmed to room temperature overnight. The reaction mixture was diluted with saturated NaHCO3 solution, concentrated, and then diluted with ethyl acetate. The organic layer was washed with sat. NaHCO3 (2×) and brine, dried over Na2SO4, filtered and concentrated to give the desired product as colorless oil (1.187 g, 76%). 1H NMR (400 MHz, CDCl3) δ 5.81 (1H, m), 5.25 (2H, m), 4.90 (1H, m), 4.25 (1H, br s), 3.67 (2H, m), 1.45 (9H, s) ppm.

후처리

  1. concentrationconcentrated
  2. additiondiluted with ethyl acetate
  3. washThe organic layer was washed with sat. NaHCO3 (2×) and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ccef6943f9134345a3d6f95c5d259238
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181271B2

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