Lithium Hydroxide → HCID 57995547, compound

HRID 385471Notes

Reaction equation

HRID 385471 reaction equation
C([O:3][C:4](=[O:32])[CH:5]([C:10]1[CH:11]=[C:12]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)[C:13]([Cl:21])=[C:14]([O:16][CH2:17][CH:18]2[CH2:20][CH2:19]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])C.[Li+].[OH-]>CO.C1COCC1.O>[Cl:21][C:13]1[C:12]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)=[CH:11][C:10]([CH:5]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:4]([OH:32])=[O:3])=[CH:15][C:14]=1[O:16][CH2:17][CH:18]1[CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57995532HCID 57995532, compound

Product 1

HCID 57995547HCID 57995547, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

The ethyl-2-(6-chloro-5-(cyclopropylmethoxy)-4′-(trifluoromethyl)biphenyl-3-yl)-4-methylpentanoate (120 mg, 0.255 mmol) dissolved in 10 mL of MeOH/THF/H2O (10 mL/10 mL/5 mL) and LiOH (30 mg, 1.2 mmol) was added. The reaction mixture was stirred at room temperature for 5 h and 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 evaporated under reduced pressure. Purification by column chromatography over silica gel (DCM:MeOH 9:1) gave 2-(6-chloro-5-(cyclopropylmethoxy)-4′-(trifluoromethyl)biphenyl-3-yl)-4-methylpentanoic acid (89 mg) as a white solid. 1H-NMR (500 MHz, CDCl3): 7.68 (d, 2H), 7.55 (d, 2H), 6.92 (s, 1H), 6.85 (s, 1H), 3.96 (d, 2H), 3.64 (t, 1H), 1.98 (m, 1H), 1.68 (m, 1H), 1.55 (m, 1H), 1.32 (m, 1H), 0.91 (d, 6H), 0.64 (m, 2H), 0.42 (m, 2H);

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. customevaporated under reduced pressure
  7. customPurification by column chromatography over silica gel (DCM:MeOH 9:1)

Sources & evidence

ORD record
ord-757aa9df54184b1da2262947b9c2595b
Source dataset
uspto-grants-2013_02
Patent number
US08367863B2

Reaction notes

Loading…