Lithium Hydroxide → HCID 57995488, compound

HRID 1183673Notes

Reaction equation

HRID 1183673 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)=[CH:6][C:5]([CH:18]([CH2:22][CH:23]2[CH2:25][CH2:24]2)[C:19]([O-:21])=[O:20])=[CH:4][C:3]=1[O:26][CH2:27][CH:28]1[CH2:30][CH2:29]1.[Li+].[OH-]>CO.C1COCC1.O>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)=[CH:6][C:5]([CH:18]([CH2:22][CH:23]2[CH2:25][CH2:24]2)[C:19]([OH:21])=[O:20])=[CH:4][C:3]=1[O:26][CH2:27][CH:28]1[CH2:30][CH2:29]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86636745HCID 86636745, compound

Product 1

HCID 57995488HCID 57995488, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

2-(6-chloro-5-(cyclopropylmethoxy)-4′-(trifluoromethyl)biphenyl-3-yl)-3-cyclopropylpropanoate (80 mg) was dissolved in 10 mL of MeOH/THF/H2O (10 mL/10 mL/5 mL) and 57 mg LiOH added. The reaction mixture was stirred at room temperature for 5 h and then concentrated under reduced pressure. Water (10 mL) was added and the reaction mixture was extracted with EtOAc (3×10 mL). The combined organic phases were dried over MgSO4, filtered and concentrated under reduced pressure. Purification by column chromatography over silica gel (hexane/EtOAc 9:1) gave compound 2-(6-chloro-5-(cyclopropylmethoxy)-4′-(trifluoromethyl)biphenyl-3-yl)-3-cyclopropylpropanoic acid (45 mg) as a white solid. 1H-NMR (500 MHz, CDCl3): 7.71 (d, 2H), 7.54 (d, 2H), 6.95 (d, 1H), 6.87 (s, 1H), 3.97 (d, 2H), 3.64 (t, 1H), 2.55 (m, 2H), 1.96 (m, 1H), 1.08 (m, 1H), 0.84 (m, 1H), 0.44 (m, 4H), 0.16 (m, 4H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionWater (10 mL) was added
  3. extractionthe reaction mixture was extracted with EtOAc (3×10 mL)
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by column chromatography over silica gel (hexane/EtOAc 9:1)

Sources & evidence

ORD record
ord-9e6c784f9d5f4ea6a4723ec6a84c4505
Source dataset
uspto-grants-2014_03
Patent number
US08664249B2

Reaction notes

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