Lithium hydroxide, monohydrate → HCID 66699619, compound

HRID 1818481Notes

Reaction equation

HRID 1818481 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][NH:18][C:19]3[CH:24]=[CH:23][C:22]([C:25](=[O:27])[CH3:26])=[C:21]([OH:28])[C:20]=3[CH3:29])=[CH:13][CH:12]=2)[CH:5]=1.O[Li].O>C1COCC1.O>[C:25]([C:22]1[CH:23]=[CH:24][C:19]([NH:18][CH2:17][C:14]2[CH:15]=[CH:16][C:11]([CH2:10][C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:30])=[O:2])=[CH:12][CH:13]=2)=[C:20]([CH3:29])[C:21]=1[OH:28])(=[O:27])[CH3:26]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 57884422HCID 57884422, compound

Product 1

HCID 66699619HCID 66699619, compoundYield 46.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 3-{4-[(4-acetyl-3-hydroxy-2-methyl-phenylamino)-methyl]-benzyl}-benzoic acid methyl ester (356 mg, 0.88 mmol) in THF (14 mL) is added a solution of LiOH.H2O (185 mg, 4.4 mmol) in H2O (7 mL). The reaction mixture is stirred at RT overnight. The reaction mixture is acidified to pH=7 and concentrated. The residue is purified by reverse phase HPLC using 90:10 to 20:80 (H2O/0.1% TFA)/CH3CN. Obtained is the title compound as a brownish solid (158 mg, 46%). LC-MS (m/e): 390 (M+1); 1H NMR (DMSO-d6) δ 13.16 (1H, s), 12.84 (1H, bs), 7.71 (2H, m), 7.43 (2H, m), 7.36 (1H, dd), 7.19 (2H, d), 7.14 (2H, d), 6.75 (1H, t), 6.05 (1H, d), 4.38 (2H, d), 3.92 (2H, s), 2.35 (3H, s), 1.94 (3H, s).

Workup

  1. concentrationconcentrated
  2. customThe residue is purified by reverse phase
  3. customObtained

Sources & evidence

ORD record
ord-fe49b6dfb80b4a5b9d24fac8d622dfd0
Source dataset
uspto-grants-2009_10
Patent number
US07598423B2

Reaction notes

Loading…