Water → HCID 69253382, compound

HRID 902761Notes

Reaction equation

HRID 902761 reaction equation
C([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][CH2:17][CH2:18][N:19]([CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[C:37]([C:41]([F:44])([F:43])[F:42])[C:36]=3[Cl:45])[CH2:20][CH:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:10]=2)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Li+].O>C1COCC1.CO>[ClH:45].[Cl:45][C:36]1[C:37]([C:41]([F:42])([F:43])[F:44])=[CH:38][CH:39]=[CH:40][C:35]=1[CH2:34][N:19]([CH2:20][CH:21]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[CH2:18][CH2:17][CH2:16][O:15][C:11]1[CH:10]=[C:9]([C:6]2([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]2)[CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 692520961(3-{3-[2-Chloro-3-trifluoromethyl-benzyl-(2,2-diphenyl-ethyl)-amino]-propoxy}-phenyl)-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 69253382HCID 69253382, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1(3-{3-[2-Chloro-3-trifluoromethyl-benzyl-(2,2-diphenyl-ethyl)-amino]-propoxy}-phenyl)-cyclopropanecarboxylic acid ethyl ester (65 mg, 0.12 mmol) in THF (1 ml) and methanol (4 ml) was added lithium hydroxide (2N aq., 1 ml). The reaction was stirred at RT overnight. Acidic water was added to neutralize the solution and the organic products were extracted into ethyl acetate, washed with brine, dried (MgSO4), and evaporated. The residue was purified by preparative HPLC (YMC CombiPrep ODS-A, 50×20 mm, 20 mL/min, A: acetonitrile B: water, A: 10 to 90% during 10 min, UV detection at 254 nm) to give 17 mg (27%) of the title compound as an oil. The oil was dissolved in methanol, and HCl in diethyl ether was added, the solvents were evaporated to form the hydrochloride salt as a solid. MS (ESI) 608.0 [M+H]+.

Workup

  1. extractionthe organic products were extracted into ethyl acetate
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by preparative HPLC (YMC CombiPrep ODS-A, 50×20 mm, 20 mL/min
  6. waitA: acetonitrile B: water, A: 10 to 90% during 10 min

Sources & evidence

ORD record
ord-04ea544eda694b918fc77f33849bc8eb
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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