Lithium hydroxide, monohydrate → HCID 69414852, compound

HRID 1296975Notes

Reaction equation

HRID 1296975 reaction equation
C[O:2][C:3](=[O:41])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][N:14]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[C:31]=2[Cl:40])[CH2:15][CH:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:6][CH:5]=1.O[Li].O>O1CCCC1.O>[Cl:40][C:31]1[C:32]([C:36]([F:37])([F:38])[F:39])=[CH:33][CH:34]=[CH:35][C:30]=1[CH2:29][N:14]([CH2:15][CH:16]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:13][CH2:12][CH2:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:41])=[O:2])=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrate2×HCID 69416683HCID 69416683, compound

Product 1

HCID 69414852HCID 69414852, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-benzoic acid methyl ester (0.20 g, 0.34 mmol) in tetrahydrofuran (7.5 mL) and H2O (2.5 mL) at ambient temperature was treated with LiOH.H2O (0.029 g, 0.68 mmol). The mixture was stirred overnight at ambient temperature. The mixture was then treated with additional LiOH.H2O (0.058 g, 1.37 mmol) and heated at 50° C. overnight. The reaction was cooled to 0° C. and was quenched with H2O (5 mL). The mixture was the acidified to a pH=2 with 1 N HCl (aq.). The mixture was then extracted three times with EtOAc, dried, filtered and concentrated in-vacuo to afford the carboxylic acid product. The acid was purified via reverse-phase HPLC (TMC CombiPrep PDS, 75×30 mm, 25 mL/min, acetonitrile:H2O, UV detection at 254 nm) to yield the title compound, 0.140 g (72%); MS (ESI) m/e 569 [M+H]+.

Workup

  1. temperatureheated at 50° C. overnight
  2. temperatureThe reaction was cooled to 0° C.
  3. customwas quenched with H2O (5 mL)
  4. extractionThe mixture was then extracted three times with EtOAc
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-6028812e92e9447791f3ea48e21fcae0
Source dataset
uspto-grants-2007_07
Patent number
US07247748B2

Reaction notes

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