Sodium Hydroxide → HCID 58553821, compound

HRID 2408158Notes

Reaction equation

HRID 2408158 reaction equation
[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]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58349494HCID 58349494, compound

Product 1

HCID 58553821HCID 58553821, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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.

Sources & evidence

ORD record
ord-64ba30f242c149028194a147be93b2c6
Source dataset
uspto-grants-2014_08
Patent number
US08809579B2

Reaction notes

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