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Methyl 4-{1-[2-tert-butoxy-1-(4-chlorophenyl)-2-oxoethyl]butyl}benzoate → HCID 58560980, 화합물

HRID 2408161
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HRID 2408161 반응식
C([O:5][C:6](=O)[CH:7]([CH:15]([C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1)[CH2:16][CH2:17][CH3:18])[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)(C)(C)C>C1COCC1>[Cl:14][C:11]1[CH:10]=[CH:9][C:8]([CH:7]([CH:15]([C:19]2[CH:20]=[CH:21][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:27][CH:28]=2)[CH2:16][CH2:17][CH3:18])[CH2:6][OH:5])=[CH:13][CH:12]=1
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반응물 1

HCID 58349494Methyl 4-{1-[2-tert-butoxy-1-(4-chlorophenyl)-2-oxoethyl]butyl}benzoate

생성물 1

HCID 58560980HCID 58560980, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 2-(4-chlorophenyl)-3-[4-(methoxycarbonyl)phenyl]hexanoic acid (prepared as described in PCT Patent Publication WO 2008/042223 A1 published on 10 Apr. 2008, 360 mg, 1.0 mmol) in anhydrous THF (10 mL) was cooled to 0° C., then borane dimethyl sulfide complex (0.3 mL, 3 mmol) was added slowly. The mixture was stirred at room temperature for five hours, then excess reagent was quenched with MeOH (2 mL). The mixture was concentrated, then the resulting residue was diluted with EtOAc (20 mL) and K2CO3 (aq). The organic layer was washed with water, dried over anhydrous Na2SO4, filtered, then concentrated. The resulting residue was purified by silica gel chromatography eluting with 10% MeOH/DCM to afford the title compound. MS (M±H)+ 347.

후처리

  1. additionborane dimethyl sulfide complex (0.3 mL, 3 mmol) was added slowly
  2. customexcess reagent was quenched with MeOH (2 mL)
  3. concentrationThe mixture was concentrated
  4. additionthe resulting residue was diluted with EtOAc (20 mL) and K2CO3 (aq)
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue was purified by silica gel chromatography
  10. washeluting with 10% MeOH/DCM

출처 및 근거

ORD 기록
ord-7c06dec85241460fbd6f6c54e9f45631
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08809579B2

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