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Sodium Hydroxide → HCID 58553821, 화합물

HRID 2408158
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HRID 2408158 반응식
[C:1]([O:5][C:6](=[O:29])[CH:7]([CH:15]([C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25]C)=[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)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6](=[O:29])[CH:7]([CH:15]([C:19]1[CH:28]=[CH:27][C:22]([C:23]([OH:25])=[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)([CH3:2])([CH3:3])[CH3:4]
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참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 58349494Methyl 4-{1-[2-tert-butoxy-1-(4-chlorophenyl)-2-oxoethyl]butyl}benzoate

생성물 1

HCID 58553821HCID 58553821, 화합물

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of methyl 4-{1-[2-tert-butoxy-1-(4-chlorophenyl)-2-oxoethyl]butyl}benzoate (prepared as described in PCT Patent Publication WO 2008/042223 A1 published on 10 Apr. 2008, 20 g, 48 mmol) in MeOH was slowly added NaOH (5.0 N in H2O, 19 mL, 95 mmol) at ambient temperature. Once all the ester starting material was consumed by LC-MS analysis, the mixture was concentrated. The residue was partitioned between EtOAc and 1N HCl (aq). The organic layer was then washed with water then saturated NaCl (aq). The organic layer was then dried over Na2SO4, filtered, then concentrated. The resulting acid was used directly for the following step. 1H NMR (400 MHz, DMSO-d6) δ 12.80 (s, 1H); 7.88 (d, J=8 Hz, 2H); 7.48-7.65 (m, 2H); 7.45-7.74 (m, 3H); 7.15 (s, 1H); 3.87 (d, J=11.6 Hz, 1H); 3.15-3.11 (m, 1H); 1.61-1.70 (m, 1H); 1.06-1.14 (m, 1H); 0.97 (s, 9H); 0.76-0.86 (m, 2H); 0.56 (t, 0.1=7.6 Hz, 3H). LC3 2.54 min. (M-tBu+H)+ 347.

후처리

  1. customat ambient temperature
  2. customOnce all the ester starting material was consumed by LC-MS analysis
  3. concentrationthe mixture was concentrated
  4. customThe residue was partitioned between EtOAc and 1N HCl (aq)
  5. washThe organic layer was then washed with water
  6. dry with materialThe organic layer was then dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customLC3 2.54 min.

출처 및 근거

ORD 기록
ord-64ba30f242c149028194a147be93b2c6
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08809579B2

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