Sodium Hydroxide → HCID 9931830, compound

HRID 750990Notes

Reaction equation

HRID 750990 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([N:15]([CH2:27][C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)[C:16]3[CH:17]=[C:18]([CH:24]=[CH:25][CH:26]=3)[C:19]([O:21]CC)=[O:20])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CCO>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([N:15]([CH2:27][C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)[C:16]3[CH:17]=[C:18]([CH:24]=[CH:25][CH:26]=3)[C:19]([OH:21])=[O:20])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12992943HCID 12992943, compound

Product 1

HCID 9931830HCID 9931830, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6.5 g of ethyl N-(3-cyclopentyloxy-4-methoxyphenyl)-N-(3-pyridylmethyl)-3-aminobenzoate in 50 mL of EtOH was treated with 10 mL of 6N NaOH. The mixture was allowed to stand for 6 hours, concentrated, and diluted with 50 mL of H2O. The aqueous mixture was extracted with 2×50 mL of ether, acidified with AcOH to pH 3, and extracted with 2×50 mL of EtOAc. The combined EtOAc fractions were washed with 25 mL of H2O and 25 mL of brine, dried (MgSO4), and concentrated. The residue was purified by chromatography over SiO2 (35 g RediSep® column) using a linear gradient of EtOAc and hexanes as eluant (50% EtOAc to 70% EtOAc over 20 minutes) to provide 4.8 g of a yellow solid product after drying in vacuo for 12 h at 60° C. 1H NMR (CDCl3) δ 11.15 (bs, 1H), 8.708.55 (m, 2H), 7.77-6.71 (m, 9H), 4.99 (s, 2H), 4.65 (p, J=3.8 Hz, 1H), 3.84 (s, 3H), 1.86-1.70 (m, 6H), 1.65-1.45 (m, 2H).

Workup

  1. concentrationconcentrated
  2. additiondiluted with 50 mL of H2O
  3. extractionThe aqueous mixture was extracted with 2×50 mL of ether
  4. extractionextracted with 2×50 mL of EtOAc
  5. washThe combined EtOAc fractions were washed with 25 mL of H2O and 25 mL of brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography over SiO2 (35 g RediSep® column)
  9. custom(50% EtOAc to 70% EtOAc over 20 minutes)

Sources & evidence

ORD record
ord-4b61f6d6912e4ac0b72f8bb1d2596a1e
Source dataset
uspto-grants-2008_07
Patent number
US07405230B2

Reaction notes

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