Triethylamine → (S)-tert-Butyl 4-((R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-((methylsulfonyl)oxy)pentyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 451847

반응식

HRID 451847 반응식
[Si:1]([O:8][CH2:9][C@H:10]([CH2:26][CH2:27][CH2:28][OH:29])[CH2:11][C@H:12]1[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[N:13]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CCN(CC)CC.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>C(Cl)Cl>[Si:1]([O:8][CH2:9][C@H:10]([CH2:26][CH2:27][CH2:28][O:29][S:38]([CH3:37])(=[O:40])=[O:39])[CH2:11][C@H:12]1[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[N:13]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58011529(S)-tert-Butyl 4-((R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-hydroxypentyl)-2,2-dimethyloxazolidine-3-carboxylate

생성물 1

HCID 58011555(S)-tert-Butyl 4-((R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-((methylsulfonyl)oxy)pentyl)-2,2-dimethyloxazolidine-3-carboxylate수율 100%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of (S)-tert-butyl 4-((R)-2-((tert-butyldimethylsilyloxy)methyl)-5-hydroxypentyl)-2,2-dimethyloxazolidine-3-carboxylate (32 g, 74.2 mmol) and Et3N (22.5 g, 226 mmol) in CH2Cl2 (400 mL) was added a solution of MsCl (10.1 g, 89 mmol) in CH2Cl2 (50 mL) at 0-5° C. After addition, the reaction mixture was allowed to warm to rt and stir for 1 hr. The reaction was washed with water (200 mL) and the aqueous layer was extracted with CH2Cl2 (3×150 mL). The combined organic layers was washed with 10% citric acid (60 mL), sat. NaHCO3 (60 mL) and brine (100 mL), then dried over Na2SO4, filtered and concentrated to give (S)-tert-butyl 4-((R)-2-((tert-butyldimethylsilyloxy)methyl)-5-(methylsulfonyloxy)pentyl)-2,2-dimethyloxazolidine-3-carboxylate (37.7 g, 100%), which was used in the next step without purification.

후처리

  1. additionAfter addition
  2. washThe reaction was washed with water (200 mL)
  3. extractionthe aqueous layer was extracted with CH2Cl2 (3×150 mL)
  4. washThe combined organic layers was washed with 10% citric acid (60 mL), sat. NaHCO3 (60 mL) and brine (100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c8e2354028da49e783e429cf32f63c15
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08487108B2

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