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Acetic Acid → ethyl 2-[(2-{(4S)-4-[(1E,3R)-3-hydroxy-4,4-dimethyl-1-octenyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl)thio]-1,3-thiazole-4-carboxylate

HRID 1888297
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HRID 1888297 반응식
[CH3:1][C:2]([CH3:30])([CH2:26][CH2:27][CH2:28][CH3:29])[C:3](=[O:25])/[CH:4]=[CH:5]/[C@H:6]1[CH2:10][O:9][C:8](=[O:11])[N:7]1[CH2:12][CH2:13][S:14][C:15]1[S:16][CH:17]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:19]=1.[BH4-].[Na+].C(O)(=O)C.O>CO>[OH:25][C@@H:3]([C:2]([CH3:1])([CH3:30])[CH2:26][CH2:27][CH2:28][CH3:29])/[CH:4]=[CH:5]/[C@H:6]1[CH2:10][O:9][C:8](=[O:11])[N:7]1[CH2:12][CH2:13][S:14][C:15]1[S:16][CH:17]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:19]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 66857555ethyl 2-[(2-{(4S)-4-[(1E)-4,4-dimethyl-3-oxo-1-octenyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl)thio]-1,3-thiazole-4-carboxylate

생성물 1

HCID 66857441ethyl 2-[(2-{(4S)-4-[(1E,3R)-3-hydroxy-4,4-dimethyl-1-octenyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl)thio]-1,3-thiazole-4-carboxylate수율 70%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of the compound 6 (124 mg) in anhydrous methanol (1.40 mL) were added sodium borohydride (10.4 mg) and a catalytic amount of acetic acid at −78° C. and the solution was stirred at the same temperature for 1 hour. After return to room temperature, to the reaction solution was added water and the solution was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated. The obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1), to give the title compound (87.2 mg) having the following physical data.

후처리

  1. extractionthe solution was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1)

출처 및 근거

ORD 기록
ord-a8e32cd44aac4bd8aaef27881b234cc8
출처 데이터셋
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08501793B2

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