Sodium Hydroxide → (3-{3-[(2,2-Diphenyl-ethyl)-(3-trifluoromethyl-benzyl)-amino]-propoxy}-phenyl)-acetic acid

HRID 881671Notes

Reaction equation

HRID 881671 reaction equation
C[O:2][C:3](=[O:41])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:27][CH:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)[CH:6]=1.[OH-].[Na+]>CO>[C:35]1([CH:28]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:27][N:15]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:24])([F:25])[F:26])[CH:18]=2)[CH2:14][CH2:13][CH2:12][O:11][C:7]2[CH:6]=[C:5]([CH2:4][C:3]([OH:41])=[O:2])[CH:10]=[CH:9][CH:8]=2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68910010(3-{3-[(2,2-Diphenyl-ethyl)-(3-trifluoromethyl-benzyl)-amino]-propoxy}-phenyl)-acetic acid methyl ester

Product 1

HCID 25184870(3-{3-[(2,2-Diphenyl-ethyl)-(3-trifluoromethyl-benzyl)-amino]-propoxy}-phenyl)-acetic acidYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (3-{3-[(2,2-Diphenyl-ethyl)-(3-trifluoromethyl-benzyl)-amino]-propoxy}-phenyl)-acetic acid methyl ester (4g). (0.37 g, 0.0007 mol) in methanol (7.5 mL) was treated with 2N NaOH (5 mL) and the mixture stirred overnight at ambient temperature. After concentration to dryness, the residue was dissolved in EtOAc (25 mL) and water was added (10 mL), the solution acidified to pH 3 with concentrated hydrochloric acid, then extracted into EtOAc (3×20 mL). The combined organic extracts were dried over Na2SO4, and then concentrated in vacuo to provide the carboxylic acid as waxy oil, which was purified by flash chromatography (9:1 CH2Cl2/MeOH) to give the desired product as oil 0.33 g in 87% yield. 1H NMR (CD3OD) δ 7.38 (d, 2H), 7.26 (t, 1H), 7.21 (m, 8H), 7.13 (t, 4H), 6.82 (d, 1H), 6.59 (s, 1H), 6.53 (d, 1H), 4.21 (t, 1H), 3.68 (s, 2H), 3.55 (t, 2H), 3.52 (s, 2H), 3.10 (d, 2H), 2.61 (t, 2H), 1.79 (t, 2H); 13C NMR (CD3OD) δ 173.7, 160.4, 145.1, 142.7, 139.3, 133.7, 130.2, 129.8, 127.3, 126.5, 124.6, 122.4, 116.5, 113.9, 66.3, 60.9, 59.7, 51.5, 51.2, 42.6, 27.9. Anal. Calcd for C33H32F3NO3: C, 72.38; H, 5.89; N, 2.56; F, 10.41. Found: C, 72.29; H, 6.09; N, 2.96; F, 10.08.

Workup

  1. concentrationAfter concentration to dryness
  2. dissolutionthe residue was dissolved in EtOAc (25 mL)
  3. additionwater was added (10 mL)
  4. extractionextracted into EtOAc (3×20 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9644130300444632a0266d066e59057b
Source dataset
uspto-grants-2015_03
Patent number
US08993628B2

Reaction notes

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