Lithium Hydroxide → HCID 70817773, compound

HRID 2405903Notes

Reaction equation

HRID 2405903 reaction equation
[CH3:1][C:2]([S:24]([CH3:27])(=[O:26])=[O:25])([CH2:8][CH2:9][N:10]1[CH:14]=[C:13]([B:15]2[O:19][C:18]([CH3:21])([CH3:20])[C:17]([CH3:23])([CH3:22])[O:16]2)[CH:12]=[N:11]1)[C:3]([O:5]CC)=[O:4].[Li+].[OH-]>C1COCC1.O>[CH3:1][C:2]([S:24]([CH3:27])(=[O:25])=[O:26])([CH2:8][CH2:9][N:10]1[CH:14]=[C:13]([B:15]2[O:19][C:18]([CH3:20])([CH3:21])[C:17]([CH3:22])([CH3:23])[O:16]2)[CH:12]=[N:11]1)[C:3]([OH:5])=[O:4]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 77931336HCID 77931336, compound

Product 1

HCID 70817773HCID 70817773, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-methyl-2-(methylsulfonyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]butanoate (28 g, 0.07 mol) in THF (100 mL) was added a solution of LiOH (4.2 g, 0.017 mol) in H2O (50 mL). The mixture was stirred at room temperature for 5 h. The THF was removed under reduced pressure and the aqueous phase was washed with EtOAc (50 mL×2) and then acidified with aqueous HCl (3 M). The solid precipitate was filtered to give the first batch of (2-methyl-2-(methylsulfonyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]butanoic acid. The mother liquid was refrigerated for 20 h, filtered to give the second batch of 2-methyl-2-(methylsulfonyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]butanoic acid. The two batches were combined the and dried to give 2-methyl-2-(methylsulfonyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]butanoic acid (13 g, 50%) as a white solid.

Workup

  1. customThe THF was removed under reduced pressure
  2. washthe aqueous phase was washed with EtOAc (50 mL×2)
  3. filtrationThe solid precipitate was filtered

Sources & evidence

ORD record
ord-507ed486b91741a188fdb95b1e2dd76a
Source dataset
uspto-grants-2014_08
Patent number
US08809333B2

Reaction notes

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