Lithium Hydroxide → HCID 68865022, compound

HRID 902690Notes

Reaction equation

HRID 902690 reaction equation
C[O:2][C:3](=[O:43])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][C@H:13]([CH3:42])[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)[CH:6]=1.[Li+].[OH-]>C1COCC1.O>[ClH:41].[Cl:41][C:32]1[C:33]([C:37]([F:38])([F:39])[F:40])=[CH:34][CH:35]=[CH:36][C:31]=1[CH2:30][N:15]([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)[CH2:14][C@@H:13]([CH3:42])[CH2:12][O:11][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([OH:43])=[O:2])[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 9938796HCID 9938796, compound

Product 1

HCID 68865022HCID 68865022, compoundYield 157.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of (R)-2-(3-{3-[[2-chloro-3-(trifluoromethyl)benzyl](2,2-diphenylethyl)amino]-2-methyl-propoxy}-phenyl)acetic acid methyl ester (22 mg, 0.0361 mmol) in THF (0.75 ml) and water (0.25 ml) was treated with LiOH (3.0 mg, 0.072 mmol). The reaction mixture was stirred overnight at RT. The reaction mixture was concentrated and 3 N HCl (aq.) was added until the pH was less than two. The aqueous layer was extracted three times with EtOAc, the combined organic layers were dried over sodium sulfate, filtered, and concentrated. The resulting amine/carboxylic acid was dissolved in Et2O (diethylether) and acidified with 1.0 M HCl/Et2O. The reaction mixture was concentrated in vacuo and dried under reduced pressure to give 18 mg (78% yield) of the title compound as a white solid. MS(ESI) 596.0(M+).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. addition3 N HCl (aq.) was added until the pH was less than two
  3. extractionThe aqueous layer was extracted three times with EtOAc
  4. dry with materialthe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe resulting amine/carboxylic acid was dissolved in Et2O (diethylether)
  8. concentrationThe reaction mixture was concentrated in vacuo
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-da7a66704f9b4c13a26ae4d7447afa69
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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