Hydrochloric Acid → HCID 68815846, 화합물

HRID 732361노트

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HRID 732361 반응식
N1C(C)=CC=CC=1C.[Si:9]([O:16]S(C(F)(F)F)(=O)=O)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].[C:24]([O:28][C:29]([N:31]1[CH2:35][C@H:34]([F:36])[CH2:33][C@@H:32]1[C@@H:37](O)[C@H:38]([CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[C:39]([N:41]1[C@@H:45]([CH:46]([CH3:48])[CH3:47])[CH2:44][O:43][C:42]1=[O:49])=[O:40])=[O:30])([CH3:27])([CH3:26])[CH3:25].Cl>ClCCl>[C:24]([O:28][C:29]([N:31]1[CH2:35][C@H:34]([F:36])[CH2:33][C@@H:32]1[C@@H:37]([O:16][Si:9]([C:12]([CH3:13])([CH3:14])[CH3:15])([CH3:10])[CH3:11])[C@H:38]([CH2:50][C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)[C:39]([N:41]1[C@@H:45]([CH:46]([CH3:47])[CH3:48])[CH2:44][O:43][C:42]1=[O:49])=[O:40])=[O:30])([CH3:26])([CH3:27])[CH3:25]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 688147272-(R)-[2-(S)-Benzyl-1-(S)-hydroxy-3-(4-(S)-isopropyl-2-oxo-oxazolidin-3-yl)-3-oxopropyl]-4-(R)-fluoropyrrolidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 68815846HCID 68815846, 화합물수율 87%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Add 2,6-lutidine (5.3 mL, 54 mmol) and tert-butyl-dimethylsilyl-trifluoromethylsulfonate (1.62 mL, 7.08 mL) to a solution of 2-(R)-[2-(S)-benzyl-1-(S)-hydroxy-3-(4-(S)-isopropyl-2-oxo-oxazolidin-3-yl)-3-oxopropyl]-4-(R)-fluoropyrrolidine-1-carboxylic acid tert-butyl ester (2.585 g, 5.4 mmol) in dichloromethane (40 mL) at −78° C. Stir 3 h, warm to room temperature, stir 5 min and cool in an ice bath. Add 1 N HCl (100 mL), wash with 1 N HCl (2×100 mL), saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with hexanes and ethyl acetate) to give the title compound as a white foam (2.779 g, 87%).

후처리

  1. stirringstir 5 min
  2. temperaturecool in an ice bath
  3. washwash with 1 N HCl (2×100 mL), saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride
  4. dry with materialdry (magnesium sulfate)
  5. concentrationconcentrate
  6. custompurify
  7. wash(silica gel chromatography, eluting with hexanes and ethyl acetate)

출처 및 근거

ORD 기록
ord-d92da758cb8c4458917dacd9d90e43b4
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585885B2

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