Lithium Hydroxide → HCID 58986250, compound

HRID 12612Notes

Reaction equation

HRID 12612 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:17]2[CH2:16][CH2:15][CH2:14][CH:13]([CH2:18][C:19]([O:21]CC)=[O:20])[C:12]=2[N:11]([CH:24]([C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=2)[CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:10]=1.[Li+].[OH-]>O1CCOCC1.O.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:17]2[CH2:16][CH2:15][CH2:14][CH:13]([CH2:18][C:19]([OH:21])=[O:20])[C:12]=2[N:11]([CH:24]([C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:41])([F:42])[F:40])=[CH:35][CH:34]=2)[CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:10]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 86761122ethyl (3-(2,4-dichlorophenyl)-1-{3-phenyl-1-[4-(trifluoromethyl)phenyl]propyl}-4,5,6,7-tetrahydro-1H-indo 1-7-yl)acetate

Product 1

HCID 58986250HCID 58986250, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

The ester from the foregoing step (0.03 g, 0.05 mmol) was dissolved in a mixture of dioxane (7 ml)/water (2 ml). Then LiOH (12 mg, 0.5 mmol) was added and the solution heated to 60° C. for 14 h. The reaction mixture was then diluted with AcOEt (20 ml), washed with 2.0N HCl (20 ml), brine (20 ml), dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with 20% AcOEt/Hexane and consequently by HPLC (gradient 60-98% CH3CN/0.1% TFA-H20) to afford 1.2 mg of the title compound; m/z (ES+) 586 (MH+); m/z (ES−) 584 (M−H+).

Workup

  1. washwashed with 2.0N HCl (20 ml), brine (20 ml)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography on silica gel eluting with 20% AcOEt/Hexane and consequently by HPLC (gradient 60-98% CH3CN/0.1% TFA-H20)

Sources & evidence

ORD record
ord-f60a963a40874eb2bc297b9753793e5a
Source dataset
uspto-grants-2010_06
Patent number
US07728022B2

Reaction notes

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