Lithium Hydroxide → (3S)-3-(3-Isoxazolyl)-3-(4-(((5-(4-(trifluoromethyl)phenyl)-2-thienyl)methyl)oxy)phenyl)propanoic acid

HRID 2235650Notes

Reaction equation

HRID 2235650 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C@H:6]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]3[S:21][C:22]([C:25]4[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=4)=[CH:23][CH:24]=3)=[CH:14][CH:13]=2)[CH2:7][C:8]([O:10]C)=[O:9])=[N:2]1.[Li+].[OH-]>C1COCC1.CO>[O:1]1[CH:5]=[CH:4][C:3]([C@H:6]([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH2:19][C:20]3[S:21][C:22]([C:25]4[CH:26]=[CH:27][C:28]([C:31]([F:34])([F:32])[F:33])=[CH:29][CH:30]=4)=[CH:23][CH:24]=3)=[CH:16][CH:17]=2)[CH2:7][C:8]([OH:10])=[O:9])=[N:2]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59300661Methyl (3S)-3-(3-isoxazolyl)-3-(4-(((5-(4-(trifluoromethyl)phenyl)-2-thienyl)methyl)oxy)phenyl)propanoate

Product 1

HCID 59300591(3S)-3-(3-Isoxazolyl)-3-(4-(((5-(4-(trifluoromethyl)phenyl)-2-thienyl)methyl)oxy)phenyl)propanoic acidYield 83%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 61.6 (0.12 mmol) in 3:1 THF/MeOH (2.8 mL) was added 1N LiOH (0.7 mL). The mixture was stirred for 1 hour at room temperature, quenched with 1N HCl (0.8 mL), and extracted with EtOAc. The combined organic layers were washed with water and brine, dried (Na2SO4), and concentrated to afford 61 (47 mg, 83%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.29 (d, 1H), 7.68 (d, 2H), 7.62 (d, 2H), 7.28 (d, 1H), 7.20 (d, 2H), 7.09 (d, 1H), 6.95 (d, 2H), 6.07 (d, 1H), 5.19 (s, 2H), 4.56 (t, 1H), 3.36 (dd, 1H), 2.99 (dd, 1H).

Workup

  1. customquenched with 1N HCl (0.8 mL)
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ee8f4e3975af4d02abd8f6507fd9aca8
Source dataset
uspto-grants-2010_05
Patent number
US07714008B2

Reaction notes

Loading…