Methanol → (s)-(-)-3-(Benzyloxycarbonyl)-4-oxazolidinecarboxylic methyl ester

HRID 2403485노트

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HRID 2403485 반응식
[CH2:1]([O:8][C:9]([N:11]1[C@H:15]([C:16]([OH:18])=[O:17])[CH2:14][O:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:23]O>>[CH3:23][O:17][C:16]([C@@H:15]1[CH2:14][O:13][CH2:12][N:11]1[C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])=[O:18]

참가 물질

4

반응물 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 688328(-)-3-(Benzyloxycarbonyl)-4-oxazolidinecarboxylic acid

생성물 1

HCID 14630870(s)-(-)-3-(Benzyloxycarbonyl)-4-oxazolidinecarboxylic methyl ester

실험 절차

To a stirred solution of (s)-(−)-3-(Benzyloxycarbonyl)-4-oxazolidinecarboxylic acid 9 (1.75 g, 6.96 mmol) in anhydrous methanol (15 mL) was added thionyl chloride (1.02 mL, 13.9 mmol) at 0° C. After 30 minutes, the ice/water bath was removed and the reaction mixture continued to be stirred at room temperature for 3.5 hours. The reaction was quenched by addition of saturated sodium bicarbonate and diluted with dichloromethane (100 mL) and water (50 mL). The mixture was separated and the aqueous layer was extracted with dichloromethane (2×50 mL). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and filtered. The solvents were removed under reduced pressure and the residue was purified by silica gel chromatography (Hexanes/AcOEt, 1.5:1) to give (s)-(−)-3-(Benzyloxycarbonyl)-4-oxazolidinecarboxylic methyl ester 10 as colorless oil (1.84 g, y=99%). 1H NMR (400 Hz, CDCl3): the compound appears as a pair of distinct rotomers. δ 7.35 (bs, 5H), 5.22-4.99 (m, 4H), 4.53-4.45 (m, 1H), 4.22-4.09 (m, 2H), 3.76 (s, 1.5H), 3.65 (s, 1.5H); MS (m/z). found 288.0 (M+Na)+.

후처리

  1. customthe ice/water bath was removed
  2. customThe reaction was quenched by addition of saturated sodium bicarbonate
  3. additiondiluted with dichloromethane (100 mL) and water (50 mL)
  4. customThe mixture was separated
  5. extractionthe aqueous layer was extracted with dichloromethane (2×50 mL)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customThe solvents were removed under reduced pressure
  10. customthe residue was purified by silica gel chromatography (Hexanes/AcOEt, 1.5:1)

출처 및 근거

ORD 기록
ord-600b70b4c6b4415a9cc79df7d10e09e5
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08802667B2

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