Sodium Hydroxide → 4-[[[2-(4-Morpholinyl)ethyl][2-[4-[[4-(2-oxazolyl)phenyl]methyl]phenoxy]ethyl]-amino]methyl]benzoic acid

HRID 1046342Notes

Reaction equation

HRID 1046342 reaction equation
[N:1]1([CH2:7][CH2:8][N:9]([CH2:31][C:32]2[CH:41]=[CH:40][C:35]([C:36]([O:38]C)=[O:37])=[CH:34][CH:33]=2)[CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]4[O:27][CH:28]=[CH:29][N:30]=4)=[CH:22][CH:21]=3)=[CH:15][CH:14]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO>[N:1]1([CH2:7][CH2:8][N:9]([CH2:31][C:32]2[CH:33]=[CH:34][C:35]([C:36]([OH:38])=[O:37])=[CH:40][CH:41]=2)[CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]4[O:27][CH:28]=[CH:29][N:30]=4)=[CH:22][CH:21]=3)=[CH:15][CH:14]=2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68484695Methyl 4-([[2-(4-morpholinyl)ethyl][2-[4-[[4-(2-oxazolyl)phenyl]methyl]phenoxy]ethyl]amino]-methyl]benzoate

Product 1

HCID 236422374-[[[2-(4-Morpholinyl)ethyl][2-[4-[[4-(2-oxazolyl)phenyl]methyl]phenoxy]ethyl]-amino]methyl]benzoic acidYield 5.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 4-[[[2-(4-morpholinyl)ethyl][2-[4-[[4-(2-oxazolyl)phenyl]methyl]phenoxy]ethyl]amino]methyl]benzoate (0.22 g, 4 mmol) in methanol (13 mL) was stirred as a 1.2 N aqueous solution of sodium hydroxide (3 mL) was added. The reaction was stirred for 17 h and concentrated. Purification of the aqueous mixture after acidification on reverse phase HPLC using a gradient of acetonitrile in water (plus 0.1% TFA) gave 0.12 g of 4-[[[2-(4-morpholinyl)ethyl][2-[4-[[4-(2-oxazolyl)phenyl]methyl]phenoxy]ethyl]-amino]methyl]benzoic acid; 1H NMR (400 MHz, DMSO-d6) δ 8.22 (s, 1H), 7.97 (m, 4H), 7.48 (d, 2H), 7.38 (m, 3H), 7.18 (d, 2H), 6.82 (d, 2H), 4.03 (t, 2H), 3.96 (s, 2H), 3.88 (s, 2H), 3.54 (m, 4H), 2.86 (t, 2H), 2.68 (t, 2H), 2.42 (m, 2H), 2.36 (m, 4H) ppm.

Workup

  1. additionwas added
  2. concentrationconcentrated
  3. customPurification of the aqueous mixture after acidification on reverse phase HPLC

Sources & evidence

ORD record
ord-e6b1e4799b194036ad8b3072a64408d4
Source dataset
uspto-grants-2013_10
Patent number
US08569303B2

Reaction notes

Loading…