Water → 3-Cyclopentyl-2-[4-(4-methyl-piperazine-1-sulfonyl)phenyl]propionic acid

HRID 2353338Notes

Reaction equation

HRID 2353338 reaction equation
C([O:3][C:4](=[O:28])[CH:5]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([N:21]2[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]2)(=[O:20])=[O:19])=[CH:14][CH:13]=1)[CH2:6][CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)C.O.[OH-].[Na+]>CO>[CH:7]1([CH2:6][CH:5]([C:12]2[CH:13]=[CH:14][C:15]([S:18]([N:21]3[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]3)(=[O:19])=[O:20])=[CH:16][CH:17]=2)[C:4]([OH:28])=[O:3])[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 444735283-Cyclopentyl-2-[4-(4-methyl-piperazine-1-sulfonyl)phenyl]propionic acid ethyl ester

Product 1

HCID 444754013-Cyclopentyl-2-[4-(4-methyl-piperazine-1-sulfonyl)phenyl]propionic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the title D compound, 3-cyclopentyl-2-[4-(4-methyl-piperazine-1-sulfonyl)-phenyl]-propionic acid ethyl ester (14 g, 0.034 mol) in methanol:water (30 mL:10 mL) and sodium hydroxide (4.11 g, 0.10 mol) is stirred at 60° C. for 8 h in an oil bath. The methanol is then removed in vacuo at 45-50° C. The residue is diluted with water (25 mL) and extracted with ether (1×40 mL). The aqueous layer is acidified to pH 5 with 3 N aqueous hydrochloric acid solution. The precipitated solid is collected by vacuum filtration, washed with water (20 mL), followed by isopropyl alcohol (20 mL). Finally, solid cake is washed with 100 mL of hexane and dried under vacuum at 40° C. for 6 h to give 3-cyclopentyl-2-[4-(4-methyl-piperazine-1-sulfonyl)-phenyl]-propionic acid as a white solid: 1H NMR (400 MHz, CDCl3) δ 1.1-2.0 (m, 11H), 2.4 (s, 3H), 2.7 (br s, 4H), 3.1 (br s, 4H), 3.6 (m, 1H), 7.5 (d, J=8.3, 2H), 7.6 (d, J=8.3, 2H); MS 381 [M+l]+.

Workup

  1. customThe methanol is then removed in vacuo at 45-50° C
  2. additionThe residue is diluted with water (25 mL)
  3. extractionextracted with ether (1×40 mL)
  4. filtrationThe precipitated solid is collected by vacuum filtration
  5. washwashed with water (20 mL)
  6. washFinally, solid cake is washed with 100 mL of hexane
  7. customdried under vacuum at 40° C. for 6 h

Sources & evidence

ORD record
ord-0f1a31fc53b34b71b71fd5c67a8e7b23
Source dataset
uspto-grants-2010_07
Patent number
US07750020B2

Reaction notes

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