Lithium Hydroxide → HCID 57965771, compound

HRID 1920595Notes

Reaction equation

HRID 1920595 reaction equation
[OH-].[Li+].C([O:5][C:6](=[O:45])[CH2:7][C:8]1([CH2:11][CH2:12][CH:13](/[CH:24]=[CH:25]/[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[O:32][CH2:33][C:34]2[CH:39]=[CH:38][C:37]([O:40][C:41]([F:44])([F:43])[F:42])=[CH:36][CH:35]=2)[CH2:14][C:15]2[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)C>C1COCC1.O>[C:6]([CH2:7][C:8]1([CH2:11][CH2:12][CH:13](/[CH:24]=[CH:25]/[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[O:32][CH2:33][C:34]2[CH:35]=[CH:36][C:37]([O:40][C:41]([F:42])([F:44])[F:43])=[CH:38][CH:39]=2)[CH2:14][C:15]2[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)([OH:45])=[O:5]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 57965763HCID 57965763, compound

Product 1

HCID 57965771HCID 57965771, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

4 mg (0.17 mmol) of lithium hydroxide are added to a solution of 50 mg (0.08 mmol) of 4-[(3E)-2-{2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]ethyl}-4-(2-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-but-3-en-1-yl]benzoic acid (enantiomer 1) in 2 ml of THF and 1 ml of water, and the mixture is stirred at 50° C. for 12 hours. After cooling, the THF is removed under reduced pressure, and the aqueous phase is adjusted to pH 4 using 1 M hydrochloric acid. The product precipitates out and is filtered off, washed with water and dried. This gives 38 mg (79% of theory) of a slightly white solid.

Workup

  1. temperatureAfter cooling
  2. customthe THF is removed under reduced pressure
  3. customThe product precipitates out
  4. filtrationis filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-42dd11b99fc844c9b5da37507deadb5a
Source dataset
uspto-grants-2012_05
Patent number
US08168821B2

Reaction notes

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