Water → 3-{2-[(2R)-2-(tert-butyldimethyl silanyloxy)-2-(4-hydroxy-3-hydroxymethyl-phenyl)ethylamino]-2-methylpropyl}benzoic acid

HRID 1866512Notes

Reaction equation

HRID 1866512 reaction equation
C[O:2][C:3](=[O:34])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][C:11]([NH:14][CH2:15][C@H:16]([O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([CH2:24][OH:25])[CH:18]=2)([CH3:13])[CH3:12])[CH:5]=1.[OH-].[Na+].O>O1CCOCC1>[Si:27]([O:26][C@H:16]([C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([CH2:24][OH:25])[CH:18]=1)[CH2:15][NH:14][C:11]([CH3:13])([CH3:12])[CH2:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[C:3]([OH:34])=[O:2])([C:30]([CH3:31])([CH3:32])[CH3:33])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 690248003-(2-[(2R)-2-(tert-butyldimethylsilanyloxy)-2-(4-hydroxy-3-hydroxymethyl-phenyl)ethylamino]-2-methylpropyl}benzoic acid methyl ester

Product 1

HCID 579783093-{2-[(2R)-2-(tert-butyldimethyl silanyloxy)-2-(4-hydroxy-3-hydroxymethyl-phenyl)ethylamino]-2-methylpropyl}benzoic acidYield 87.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-{2-[(2R)-2-(tert-butyldimethylsilanyloxy)-2-(4-hydroxy-3-hydroxymethyl-phenyl)ethylamino]-2-methylpropyl}benzoic acid methyl ester (Preparation 36) (1.50 g, 3.08 mmol), aqueous sodium hydroxide solution (5M, 3.07 ml, 15.0 mmol), water (2 ml) and dioxane (20 ml) were stirred at room temperature for 18 hours. The solvent was removed in vacuo and the residue dissolved in water (30 ml) and acidified with aqueous hydrochloric acid (1N, 15.38 ml). The resulting white precipitate was filtered off and dried in vacuo for 72 hours to furnish the title compound as a white solid (1.28 g). 1H NMR (400 MHz, CD3OD) δ=7.88 (1H, d), 7.81 (1H, bs), 7.38-7.28 (3H, m), 7.10 (1H, dd), 6.77 (1H, d), 4.92 (1H, m, partially under solvent peak), 4.61 (2H, dd), 3.23-3.12 (2H, m), 2.95 (2H, dd), 1.08 (6H, s), 0.81 (9H, s), −0.04 (3H, s), −0.15 (3H, s). LRMS (electrospray) m/z 474 [M+H]+

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in water (30 ml)
  3. filtrationThe resulting white precipitate was filtered off
  4. customdried in vacuo for 72 hours

Sources & evidence

ORD record
ord-4e1353e28a0149079dc2ebfb1c46e4ce
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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