2,2-Dimethoxypropane → tert-butyl (4S)-4-(2-methoxy-2-oxo-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylate

HRID 1254362노트

반응식

HRID 1254362 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:15][OH:16])[CH2:10][C:11]([O:13][CH3:14])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO[C:19](OC)([CH3:21])[CH3:20]>CC(C)=O.B(F)(F)F.CCOCC>[CH3:14][O:13][C:11](=[O:12])[CH2:10][C@H:9]1[CH2:15][O:16][C:19]([CH3:21])([CH3:20])[N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7]

참가 물질

5

반응물 2

HCID 64952,2-DimethoxypropaneHCID 54573797Methyl (S)-3-(Boc-amino)-4-hydroxybutanoate

생성물 1

HCID 10923729tert-butyl (4S)-4-(2-methoxy-2-oxo-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylate수율 92%

시약·촉매·용매 2

HCID 8000Boron trifluoride etherate촉매HCID 180Acetone용매

실험 절차

To a solution of (S)-methyl 3-(tert-butoxycarbonylamino)-4-hydroxybutanoate (7.0 g, 30.0 mmol) in acetone (90 mL), there was added 2,2-dimethoxypropane (37 mL, 300 mmol) followed by BF3.Et2O (0.11 mL, 0.9 mmol). The resulting solution was stirred at rt overnight. Solvents were removed under vacuum, and the residue was redissolved in ether (100 mL), washed with sat'd NaHCO3 (20 mL). Upon concentrating under vacuum, the residue was purified by flash column chromatography to give (S)-tert-butyl 4-(2-methoxy-2-oxoethyl)-2,2-dimethyloxazolidine-3-carboxylate (7.51 g, 92%). MS m/z 296 (M+Na+).

후처리

  1. customSolvents were removed under vacuum
  2. dissolutionthe residue was redissolved in ether (100 mL)
  3. washwashed with sat'd NaHCO3 (20 mL)
  4. concentrationUpon concentrating under vacuum
  5. customthe residue was purified by flash column chromatography

출처 및 근거

ORD 기록
ord-6316ef4bf1f34b8c8565447ccd5f4e21
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455521B2

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