Hydrochloric Acid → HCID 70817707, compound

HRID 2405927Notes

Reaction equation

HRID 2405927 reaction equation
[CH3:1][C@@:2]([S:21]([CH3:24])(=[O:23])=[O:22])([CH2:8][CH2:9][N:10]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]=[N:11]1)[C:3]([O:5]CC)=[O:4].[Li+].[OH-].Cl>C1COCC1.O>[CH3:1][C@@:2]([S:21]([CH3:24])(=[O:22])=[O:23])([CH2:8][CH2:9][N:10]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]=[N:11]1)[C:3]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86710239HCID 86710239, compound

Product 1

HCID 70817707HCID 70817707, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of ethyl (2R)-2-methyl-2-(methylsulfonyl)-4-(4-phenyl-1H-pyrazol-1-yl)butanoate (1.22 g, 3.48 mmol, 1 eq) in THF-H2O (15 mL:15 mL) was added LiOH (0.258 g, 10.4 mmol, 3 eq). The mixture was allowed to stir at RT overnight. The mixture was acidified with 1M HCl and extracted with EtOAc. The organic layers were combined, dried (MgSO4), filtered and concentrated to give (2R)-2-methyl-2-(methylsulfonyl)-4-(4-phenyl-1H-pyrazol-1-yl)butanoic acid (0.855 g, 76 yield). 1H NMR (400 MHz, DMSO-d6) δ 8.20 (s, 1H), 7.86 (s, 1H), 7.53 (d, J=7.4 Hz, 2H), 7.32 (t, J=7.7 Hz, 2H), 7.15 (s, 1H), 4.35-4.23 (m, 1H), 4.20-4.08 (m, 1H), 3.11 (s, 3H), 2.71-2.57 (m, 1H), 2.38-2.25 (m, 1H), 1.50 (s, 3H). LC-MS M+H+323.1.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-29c78306e7a8445482e2a7bc66532cba
Source dataset
uspto-grants-2014_08
Patent number
US08809333B2

Reaction notes

Loading…