Lithium Hydroxide → HCID 86603444, compound

HRID 229124Notes

Reaction equation

HRID 229124 reaction equation
C[O:2][C:3](=[O:43])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[C:32]=2[Cl:41])[CH2:16][CH:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:7]([Cl:42])[CH:6]=1.C1COCC1.[Li+].[OH-]>O>[ClH:41].[Cl:42][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([OH:43])=[O:2])[CH:10]=[CH:9][C:8]=1[O:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[C:32]=1[Cl:41])[CH2:16][CH:17]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 57757106HCID 57757106, compound

Product 1

HCID 86603444HCID 86603444, compoundYield 175.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (3-chloro-4-{3-[(2-chloro-3-trifluoromethyl-benzyl)-2,2-diphenylethyl-amino]-propoxy}-phenyl)-acetic acid methyl ester (42.8 mg, 0.068 mmol) and THF (2.5 mL) and H2O (0.8 mL), LiOH (3.4 mg, 0.14 mmol) was added and the reaction mixture was stirred for 12 h. The mixture was concentrated and H2O was added. The mixture was acidified with 1N HCl, extracted several times with EtOAc, and concentrated. The resulting oil was diluted in Et2O and acidified with 1.0 M HCl/Et2O. The mixture was then concentrated to give the product as a white solid (38.9 mg, 88%). MS(ES) m/e 616.2 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated
  2. additionH2O was added
  3. extractionextracted several times with EtOAc
  4. concentrationconcentrated
  5. additionThe resulting oil was diluted in Et2O
  6. concentrationThe mixture was then concentrated

Sources & evidence

ORD record
ord-0f2d3328e99f494a880934b02afe122a
Source dataset
uspto-grants-2009_07
Patent number
US07560586B2

Reaction notes

Loading…