Sodium Hydroxide → HCID 68906853, compound

HRID 881675Notes

Reaction equation

HRID 881675 reaction equation
C[O:2][C:3](=[O:30])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14][NH:15][CH2:16][CH:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=1.[OH-].[Na+]>CO>[C:24]1([CH:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:16][NH:15][CH2:14][CH2:13][CH2:12][O:11][C:7]2[CH:6]=[C:5]([CH2:4][C:3]([OH:30])=[O:2])[CH:10]=[CH:9][CH:8]=2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68906807{3-[3-(2,2-Diphenyl-ethylamino)-propoxy]-phenyl}-acetic acid methyl ester

Product 1

HCID 68906853HCID 68906853, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of {3-[3-(2,2-Diphenyl-ethylamino)-propoxy]-phenyl}-acetic acid methyl ester (3) (0.03 g, 0.000074 mol) in methanol (3 mL) was treated with 2N NaOH (2 mL) and the mixture stirred overnight at ambient temperature. After concentration to dryness, the residue was dissolved in EtOAc (15 mL) and water was added (5 mL), the solution acidified to pH 3 with concentrated hydrochloric acid, then extracted into EtOAc (3×15 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 a solid 0.025 g in 83% yield. Crystallization of the solid from EtOAc gave white crystals, mp: 49.1° C. 1HNMR (CD3OD) δ 7.17 (m, 1H), 6.80 (d, 1H), 6.78 (d, 1H), 6.64 (s, 1H), 4.12 (t, 1H), 3.56 (s, 2H), 3.49 (t, 2H), 3.12 (d, 2H), 2.66 (t, 2H), 1.72 (t, 2H); 13C NMR (CD3OD) δ 176.0, 160.1, 143.5, 137.9, 130.4, 129.9, 129.1, 128.0, 122.9, 116.6, 113.9, 65.9, 60.1, 54.8, 51.9, 42.6, 26.3. Anal. Calcd for C25H27NO3. 2H2O: C, 70.56; H, 6.40; N, 3.29. Found: C, 70.58; H, 6.28; N, 3.20.

Workup

  1. concentrationAfter concentration to dryness
  2. dissolutionthe residue was dissolved in EtOAc (15 mL)
  3. additionwater was added (5 mL)
  4. extractionextracted into EtOAc (3×15 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-597f2ca877724b8abecc7ca6d5991166
Source dataset
uspto-grants-2015_03
Patent number
US08993628B2

Reaction notes

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