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

HRID 881670Notes

Reaction equation

HRID 881670 reaction equation
C[O:2][C:3](=[O:38])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:24][CH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([I:23])[CH:18]=2)[CH:6]=1.[OH-].[Na+]>CO>[C:26]1([CH:25]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:24][N:15]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([I:23])[CH:18]=2)[CH2:14][CH2:13][CH2:12][O:11][C:7]2[CH:6]=[C:5]([CH2:4][C:3]([OH:38])=[O:2])[CH:10]=[CH:9][CH:8]=2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68910942(3-{3-[(2,2-Diphenyl-ethyl)-(3-iodo-benzyl)-amino]-propoxy}-phenyl)-acetic acid methyl ester

Product 1

HCID 68908945(3-{3-[(2,2-Diphenyl-ethyl)-(3-iodo-benzyl)-amino]-propoxy}-phenyl)-acetic acidYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (3-{3-[(2,2-Diphenyl-ethyl)-(3-iodo-benzyl)-amino]-propoxy}-phenyl)-acetic acid methyl ester (4f). (0.5 g, 0.0008 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 0.32 g in 67% yield. 1H NMR (CD3OD) δ 7.92 (s, 1H), 7.53 (d, 2H), 7.27 (m, 8H), 7.19 (t, 2H), 6.93 (t, 1H), 6.88 (d, 1H), 6.67 (s, 1H), 6.64 (d, 1H), 4.25 (t, 1H), 3.70 (s, 2H), 3.65 (t, 2H), 3.58 (s, 2H), 3.16 (d, 2H), 2.69 (t, 2H), 1.86 (t, 2H); 13C NMR (CD3OD) δ 175.7, 160.4, 144.8, 144.7, 143.2, 139.3, 137.3, 137.2, 137.1, 131.0, 130.9, 130.4, 129.5, 129.3, 127.4. 122.5, 122.4, 116.6, 114.3, 94.9, 66.5, 60.7, 59.5, 51.7, 50.9, 42.2, 27.7. Anal. Calcd for C32H32INO3.H2O: C, 61.62; H, 5.17; I, 20.34; N, 2.25. Found: C, 61.70; H, 5.06; I, 20.68; N, 2.74.

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-a7090d9dfcbd417c82cf3fb45475c0c3
Source dataset
uspto-grants-2015_03
Patent number
US08993628B2

Reaction notes

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