Sodium Hydroxide → HCID 23508819, compound

HRID 1884273Notes

Reaction equation

HRID 1884273 reaction equation
C[O:2][C:3](=[O:42])[CH2:4][CH2:5][NH:6][C:7](=[O:41])[C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:40])[CH:15]([C:29]2[CH:34]=[CH:33][C:32]([O:35][C:36]([F:39])([F:38])[F:37])=[CH:31][CH:30]=2)[CH2:16][C:17]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:21][CH:20]=2)=[O:18])=[CH:10][CH:9]=1.[OH-].[Na+]>C(O)C>[C:25]([C:22]1[CH:23]=[CH:24][C:19]([C:17](=[O:18])[CH2:16][CH:15]([C:29]2[CH:30]=[CH:31][C:32]([O:35][C:36]([F:38])([F:39])[F:37])=[CH:33][CH:34]=2)[C:14]([C:11]2[CH:12]=[CH:13][C:8]([C:7]([NH:6][CH2:5][CH2:4][C:3]([OH:42])=[O:2])=[O:41])=[CH:9][CH:10]=2)=[O:40])=[CH:20][CH:21]=1)([CH3:28])([CH3:26])[CH3:27]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67483251HCID 67483251, compound

Product 1

HCID 23508819HCID 23508819, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-{4-[4-(4-tert-Butylphenyl)-4-oxo-2-(4-trifluoromethoxyphenyl)butyryl]benzoylamino}propionic acid methyl ester (12 g, 21 mmol) was dissolved in ethanol 96% (250 mL), added 4N NaOH (31.2 mL, 125 mmol), and stirred for 2 h 45 min. The reaction mixture was concentrated in vacuo and the residue suspended in water (150 mL) and added hydrochloric acid (4N, 34 mL) to pH 1-2. After 1 h the precipitate was filtered and washed carefully with water and dried. The residue was purified by preparative HPLC using acetonitrile (gradient from 42% to 97.5%), water and TFA (2.5%) as eluent to afford 4.7 g of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionadded hydrochloric acid (4N, 34 mL) to pH 1-2
  3. filtrationAfter 1 h the precipitate was filtered
  4. washwashed carefully with water
  5. customdried
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-1c30b2a6da994028a75e33f596584ad1
Source dataset
uspto-grants-2004_07
Patent number
US06762318B2

Reaction notes

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