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Ammonium Chloride → (5R)-3-[4-(2-Benzyloxy-4-ethyl-phenoxy)-3-fluoro-phenyl]-5-hydroxymethyl-oxazolidin-2-one

HRID 1023955
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HRID 1023955 반응식
C([O:8][C:9](=[O:35])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH3:25])=[CH:20][C:19]=2[O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:13]([F:34])[CH:12]=1)C1C=CC=CC=1.C([Li])CCC.[C:41](OC[C@@H]1OC1)(=[O:45])[CH2:42][CH2:43]C.[NH4+].[Cl-]>C1COCC1>[CH2:27]([O:26][C:19]1[CH:20]=[C:21]([CH2:24][CH3:25])[CH:22]=[CH:23][C:18]=1[O:17][C:14]1[CH:15]=[CH:16][C:11]([N:10]2[CH2:43][C@H:42]([CH2:41][OH:45])[O:8][C:9]2=[O:35])=[CH:12][C:13]=1[F:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1
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참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 2724536(2R)-Oxiran-2-ylmethyl butanoateHCID 59191307[4-(2-Benzyloxy-4-ethyl-phenoxy)-3-fluoro-phenyl]-carbamic acid benzyl esterHCID 178418339Butyllithium

생성물 1

HCID 59191330(5R)-3-[4-(2-Benzyloxy-4-ethyl-phenoxy)-3-fluoro-phenyl]-5-hydroxymethyl-oxazolidin-2-one수율 52%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of [4-(2-Benzyloxy-4-ethyl-phenoxy)-3-fluoro-phenyl]-carbamic acid benzyl ester (0.31 mmol; 145 mg), under argon, in dry THF cooled to −78° C., was added n-Butyl lithium 2.3M in THF (0.46 mmol; 200 μL). the reaction mixture was stirred ten minutes and (R)-glycidyl butyrate (0.34 mmol; 48 μL) was added. The reaction was stirred overnight with slow warming to room temperature. The mixture was treated with saturated NH4Cl and extracted with ethyl acetate. Combined organic phases were dried over Na2SO4 and concentrated in vacuo. The title compound (70 mg; 52%) was obtained as . . . after purification by preparative TLC (eluant: dichloromethane/methanol: 95/5).

후처리

  1. stirringThe reaction was stirred overnight
  2. extractionextracted with ethyl acetate
  3. dry with materialCombined organic phases were dried over Na2SO4
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-bf10dfecd0dc4717aa869f6bc015d994
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08722746B2

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