Lithium Hydroxide → HCID 70817544, compound

HRID 2405908Notes

Reaction equation

HRID 2405908 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][N:10]([CH2:12][CH2:13][C@@:14]([CH3:24])([S:20]([CH3:23])(=[O:22])=[O:21])[C:15]([O:17]CC)=[O:16])[CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[Li+].[OH-]>CO.C1COCC1.O>[C:1]1([C:7]2[CH:8]=[N:9][N:10]([CH2:12][CH2:13][C@@:14]([CH3:24])([S:20]([CH3:23])(=[O:21])=[O:22])[C:15]([OH:17])=[O:16])[CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86710226HCID 86710226, compound

Product 1

HCID 70817544HCID 70817544, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of ethyl (2R)-4-[4-(cyclohex-1-en-1-yl)-1H-pyrazol-1-yl]-2-methyl-2-(methylsulfonyl)butanoate (370 mg, 1.04 mmol, 1.0 eq) in MeOH/THF (3 mL:3 mL) was added LiOH (52.5 mg, 2.19 mmol, 2.1 eq) in H2O (1.5 mL) and the mixture allowed to stir at RT overnight. The mixture was diluted with 5 mL of H2O and washed with Et2O. The aqueous layer was then acidified with 1 M HCl which precipitated out a white solid. The solid was filtered off and washed with heptane to give (2R)-4-[4-(cyclohex-1-en-1-yl)-1H-pyrazol-1-yl]-2-methyl-2-(methylsulfonyl)butanoic acid (339 mg, 99.5% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ 7.75-7.66 (m, 1H), 7.41-7.35 (m, 1H), 6.05-5.96 (m, 1H), 4.78-4.59 (m, 1H), 4.55-4.38 (m, 1H), 3.14 (s, 3H), 2.77-2.64 (m, 1H), 2.51-2.37 (m, 1H), 2.28-2.19 (m, 2H), 2.18-2.06 (m, 2H), 1.80-1.69 (m, 2H), 1.64 (s, 5H). LC-MS M+H+327.1.

Workup

  1. washwashed with Et2O
  2. customprecipitated out a white solid
  3. filtrationThe solid was filtered off
  4. washwashed with heptane

Sources & evidence

ORD record
ord-cc396b0eacf440e8b8855eebcfea6092
Source dataset
uspto-grants-2014_08
Patent number
US08809333B2

Reaction notes

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