Water → HCID 53246981, compound

HRID 1189539Notes

Reaction equation

HRID 1189539 reaction equation
[C:1]([C:3]1[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)(=[O:17])=[O:16])=[C:6]([CH3:23])[N:5]([CH2:24][C:25]([O:27]CC)=[O:26])[C:4]=1[CH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1)#[N:2].O.[OH-].[Li+].O>O1CCCC1.CO>[C:1]([C:3]1[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15]([N:18]2[CH2:19][CH2:20][CH2:21][CH2:22]2)(=[O:17])=[O:16])=[C:6]([CH3:23])[N:5]([CH2:24][C:25]([OH:27])=[O:26])[C:4]=1[CH:30]1[CH2:31][CH2:32][CH2:33][CH2:34]1)#[N:2]

Participants

6

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 53246146ethyl 2-(3-cyano-2-cyclopentyl-5-methyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate

Product 1

HCID 53246981HCID 53246981, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

General procedure I was followed using ethyl 2-(3-cyano-2-cyclopentyl-5-methyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (747 mg, 1.55 mmol) and lithium hydroxide monohydrate (130 mg, 3.09 mmol) in tetrahydrofuran (9.3 mL), methanol (3.1 mL), and water (3.1 mL). The product 2-(3-cyano-2-cyclopentyl-5-methyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetic acid (685 mg, 1.50 mmol, 97% yield) was isolated as a tan solid. 1H NMR (400 MHz, CDCl3) δ (ppm): 7.99 (dd, 1H), 7.42 (ddd, 1H), 7.31 (dd, 1H), 7.00 (d, 1H), 4.65 (s, 2H), 4.30 (s, 2H), 3.32-3.36 (m, 4H), 2.94 (m, 1H), 1.87-2.04 (m, 13H, composite of multiple shifts), 1.59-1.70 (m, 2H).

Sources & evidence

ORD record
ord-9b985362368d4715a592fde74955cfce
Source dataset
uspto-grants-2014_03
Patent number
US08674115B2

Reaction notes

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