Lithium Hydroxide → HCID 58787883, compound

HRID 1375926Notes

Reaction equation

HRID 1375926 reaction equation
C([O:4][CH2:5][C:6]([NH:34]C(=O)C)([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:30]=[C:29]([CH2:31][CH2:32][CH3:33])[O:28][N:27]=3)=[CH:22][CH:21]=2)=[CH:16][CH:15]=1)[CH2:7][O:8]C(=O)C)(=O)C.[Li+].[OH-]>C1COCC1.O>[NH2:34][C:6]([CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:30]=[C:29]([CH2:31][CH2:32][CH3:33])[O:28][N:27]=3)=[CH:22][CH:21]=2)=[CH:18][CH:19]=1)([CH2:7][OH:8])[CH2:5][OH:4]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 69427789HCID 69427789, compound

Product 1

HCID 58787883HCID 58787883, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Acetic acid 2-acetoxymethyl-2-acetylamino-4-[4′-(5-propyl-isoxazol-3-yl)-biphenyl-4-yl]butyl ester (0.1 mmol) is dissolved in THF (1 mL) and treated with 2 N LiOH aqueous solution (0.5 mL). The resulting mixture is stirred at reflux for 1 h and diluted with H2O (10 mL). It is then extracted with EtOAc (3×5 mL) and the combined organic phase is washed with brine and dried over Na2SO4. After concentrated, the crude product is purified with LC-MS to give the desired product as a white solid. 1H NMR (400 MHz, CD3OD) δ 7.86 (d, J=8.4 Hz, 2H), 7.70 (d, J=8.4 Hz, 2H), 7.58 (d, J=8.2 Hz, 2H), 7.33 (d, J=8.2 Hz, 2H), 3.53 (q, J=11.0 Hz, 4H), 2.81 (t, J=7.4 Hz, 2H), 2.71 (m, 2H), 1.79 (m, 4H), 1.04 (t, J=7.4 Hz, 3H). MS: (ES+): 381.2 (M+1)+.

Workup

  1. temperatureat reflux for 1 h
  2. extractionIt is then extracted with EtOAc (3×5 mL)
  3. washthe combined organic phase is washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationAfter concentrated
  6. customthe crude product is purified with LC-MS

Sources & evidence

ORD record
ord-6619c225712a4873b542324e56907856
Source dataset
uspto-grants-2007_01
Patent number
US07169817B2

Reaction notes

Loading…