Lithium Hydroxide → HCID 11634144, compound

HRID 1727043Notes

Reaction equation

HRID 1727043 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([S:14]([N:17]3[CH2:22][CH2:21][N:20]([C:23]4[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=4)[CH2:19][CH2:18]3)(=[O:16])=[O:15])[CH:11]=2)[CH2:6]1.[Li+].[OH-]>C1COCC1>[F:32][C:29]([F:30])([F:31])[C:26]1[CH:27]=[CH:28][C:23]([N:20]2[CH2:19][CH2:18][N:17]([S:14]([C:10]3[CH:11]=[C:12]4[C:7](=[CH:8][CH:9]=3)[CH2:6][CH:5]([CH2:4][C:3]([OH:33])=[O:2])[CH2:13]4)(=[O:15])=[O:16])[CH2:22][CH2:21]2)=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57565317HCID 57565317, compound

Product 1

HCID 11634144HCID 11634144, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

{5-[4-(4-Trifluoromethyl-phenyl)-piperazine-1-sulfonyl]-indan-2-yl}-acetic acid methyl ester (118 mg, 0.245 mmol) was dissolved in THF (10 mL). To this solution was added 1M LiOH (5 mL) and was stirred at room temperature for 3 h. TLC indicated that the reaction was complete. The reaction mixture was then quenched with Dowex 50WX4-50 until neutral and then filtered to afford pure {5-[4-(4-trifluoromethyl-phenyl)-piperazine-1-sulfonyl]-indan-2-yl}-acetic acid (112 mg, 98%) as a white solid. The product can be further purified by silica gel flash column chromatography (dichloromethane/MeOH/AcOH 95:5:0.1). 1H NMR (400 MHz, MeOH-d4) 7.60 (s, 1H), 7.56 (d, 1H), 7.45 (d, 2H), 7.41 (d, 1H), 7.00 (d, 2H), 3.32 (m, 4H), 3.22 (m, 2H), 3.17 (m, 4H), 2.88 (m, 1H), 2.72 (m, 2H), 2.47 (d, 2H); LCMS: 468.8 (M+1)+.

Workup

  1. customThe reaction mixture was then quenched with Dowex 50WX4-50 until neutral and
  2. filtrationthen filtered

Sources & evidence

ORD record
ord-f967c38be432466baa344b4ecf50cb27
Source dataset
uspto-grants-2009_02
Patent number
US07494999B2

Reaction notes

Loading…