Hydrochloric Acid → 5-[(3-Cyclopentylpropanoyl)(4-{[(4-phenoxybenzyl)amino]carbonyl}-benzyl)amino]-2-hydroxybenzoic acid

HRID 902781Notes

Reaction equation

HRID 902781 reaction equation
[CH:1]1([CH2:6][CH2:7][C:8]([N:10]([CH2:24][C:25]2[CH:47]=[CH:46][C:28]([C:29]([NH:31][CH2:32][C:33]3[CH:38]=[CH:37][C:36]([O:39][C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)=[CH:35][CH:34]=3)=[O:30])=[CH:27][CH:26]=2)[C:11]2[CH:23]=[CH:22][C:14]3[O:15]C(C)(C)[O:17][C:18](=[O:19])[C:13]=3[CH:12]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>CCO>[CH:1]1([CH2:6][CH2:7][C:8]([N:10]([CH2:24][C:25]2[CH:47]=[CH:46][C:28]([C:29]([NH:31][CH2:32][C:33]3[CH:34]=[CH:35][C:36]([O:39][C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)=[CH:37][CH:38]=3)=[O:30])=[CH:27][CH:26]=2)[C:11]2[CH:23]=[CH:22][C:14]([OH:15])=[C:13]([CH:12]=2)[C:18]([OH:19])=[O:17])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 586936964-{[(3-cyclopentylpropanoyl)(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-6-yl)amino]methyl}-N-(4-phenoxybenzyl)benzamide

Product 1

HCID 114788675-[(3-Cyclopentylpropanoyl)(4-{[(4-phenoxybenzyl)amino]carbonyl}-benzyl)amino]-2-hydroxybenzoic acidYield 85.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-{[(3-cyclopentylpropanoyl)(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-6-yl)amino]methyl}-N-(4-phenoxybenzyl)benzamide (200 mg) in EtOH (3 mL) was added an aqueous solution (0.071 mL, 1N). The mixture was heated at 70° C. for 3 h. After cooling to rt, an aqueous solution of HCl (2 mL, 1N) was added and the resulting reaction mixture was extracted (EtOAc). The combined organic layers were washed with water, brine, dried over MgSO4, filtered and evaporated to give the title compound as a white powder (160 mg, 85%). 1H NMR (DMSO-d) δ 8.99 (t, J=6.0 Hz, 1H), 7.82 (d, J=8.2 Hz, 2H), 7.50 (d, J=2.6 Hz, 1H), 7.42-7.06 (m, 8H), 7.03-6.89 (m, 5H), 4.85 (s, 2H), 4.45 (s, 1H), 4.43 (s, 1H), 3.40 (brs, 1H), 2.05 (t, J=7.5 Hz, 2H), 1.70-1.32 (m, 9H), 1.00-0.81 (m, 2H). M+(ESI): 593.0; M−(ESI): 591.0. HPLC, Rt: 4.9 min purity: 99.3%).

Workup

  1. temperatureAfter cooling to rt
  2. customthe resulting reaction mixture
  3. extractionwas extracted (EtOAc)
  4. washThe combined organic layers were washed with water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-de69817435fa4df88db5b3693fe67225
Source dataset
uspto-grants-2008_04
Patent number
US07365225B2

Reaction notes

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