Sodium Hydroxide → HCID 68906705, compound

HRID 881666Notes

Reaction equation

HRID 881666 reaction equation
C[O:2][C:3](=[O:39])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:25][CH:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=2[F:24])[CH:6]=1.[OH-].[Na+]>CO>[C:33]1([CH:26]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:25][N:15]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=2[F:24])[CH2:14][CH2:13][CH2:12][O:11][C:7]2[CH:6]=[C:5]([CH2:4][C:3]([OH:39])=[O:2])[CH:10]=[CH:9][CH:8]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68911934HCID 68911934, compound

Product 1

HCID 68906705HCID 68906705, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (3-{3-[(2,2-Diphenyl-ethyl)-(2,3-difluoro-benzyl)-amino]-propoxy}-phenyl)-acetic acid methyl ester (4b). (0.83 g, 0.0016 mol) in methanol (7.5 mL) was treated with 2N NaOH (5.0 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. Solidification of the waxy oil from EtOAc gave white solid (5a) 0.73 g in 88% yield, mp: 148.4° C. 1H NMR (CD3OD) δ 7.18 (m, 1H), 6.99 (m, 1H), 6.81 (d, 2H), 6.76 (m, 1H), 6.72 (s, 1H), 6.55 (d, 1H), 4.17 (t, 1H), 3.67 (s, 2H), 3.55 (s, 2H), 3.54 (d, 2H), 3.07 (d, 2H), 2.62 (t, 2H), 1.77 (t, 2H); 13C NMR (CD3OD) δ 175.6, 160.5, 152.7, 151.5, 149.5, 149.4, 145.1, 137.3, 130.3, 130.1, 129.1, 127.6, 125.0, 124.9, 122.4, 129.3, 116.6, 114.1, 66.0, 60.9, 52.2, 51.3, 51.1, 42.2, 28.0. Anal. Calcd for C32H31F2NO3.21/2H2O: C, 68.55; H, 5.57; N, 2.50; F, 6.77. Found: C, 68.62; H, 5.27; N, 2.28; F, 6.52.

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-adc6215070c246dd87013412731f5c68
Source dataset
uspto-grants-2015_03
Patent number
US08993628B2

Reaction notes

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