Sodium Hydroxide → HCID 68910989, compound

HRID 881674Notes

Reaction equation

HRID 881674 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]=[C:21]([O:23][CH3:24])[CH:20]=[C:19]([O:25][CH3:26])[CH:18]=2)[CH:6]=1.[OH-].[Na+]>CO>[C:29]1([CH:28]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:27][N:15]([CH2:16][C:17]2[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[C:19]([O:25][CH3:26])[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:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68908958HCID 68908958, compound

Product 1

HCID 68910989HCID 68910989, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (3-{3-[(2,2-Diphenyl-ethyl)-(3,5-dimethoxy-benzyl)-amino]-propoxy}-phenyl)-acetic acid methyl ester (4j). (0.26 g, 0.00047 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 (3×20 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 0.23 g in 92% yield. Solidification of the waxy oil from pet. ether gave white solid (5j), mp: 44.4° C. 1H NMR (CD3OD) δ 7.19 (d, 9H), 7.11 (m, 2H), 6.82 (d, 1H), 6.60 (s, 1H), 6.56 (d, 1H), 6.30 (s, 2H), 6.27 (s, 1H), 4.21 (t, 1H), 3.62 (t, 2H), 3.60 (s, 2H), 3.57 (s, 6H), 3.52 (s, 2H), 3.16 (d, 2H), 2.68 (t, 2H), 1.81 (t, 2H); 13C NMR (CD3OD) δ 176.0, 162.1, 160.4, 144.8, 143.7, 137.6, 130.2, 129.4, 129.3, 127.4, 122.5, 116.5, 114.1, 107.9, 100.6, 66.7, 60.8, 60.6, 55.7, 52.0, 50.9, 42.5, 27.7. Anal. Calcd for C34H37NO5: C, 75.67; H, 6.91; N, 2.60. Found: C, 75.62; H, 6.94; N, 2.42.

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 (3×20 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-318ba8f975e5497185e0e93d899e4a6b
Source dataset
uspto-grants-2015_03
Patent number
US08993628B2

Reaction notes

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