Sodium Hydroxide → 4-((N,N-diethylsulfamoyl)methyl)-2-ethylcyclopentanecarboxylic acid

HRID 1969701Notes

Reaction equation

HRID 1969701 reaction equation
[CH2:1]([N:3]([CH2:20][CH3:21])[S:4]([CH2:7][CH:8]1[CH2:12][CH:11]([C:13]([O:15]CC)=[O:14])[CH:10]([CH2:18][CH3:19])[CH2:9]1)(=[O:6])=[O:5])[CH3:2].[OH-].[Na+]>>[CH2:20]([N:3]([CH2:1][CH3:2])[S:4]([CH2:7][CH:8]1[CH2:12][CH:11]([C:13]([OH:15])=[O:14])[CH:10]([CH2:18][CH3:19])[CH2:9]1)(=[O:6])=[O:5])[CH3:21]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 58557908ethyl 4-((N,N-diethylsulfamoyl)methyl)-2-ethylcyclopentanecarboxylate

Product 1

HCID 585578104-((N,N-diethylsulfamoyl)methyl)-2-ethylcyclopentanecarboxylic acidYield 72.1%

Procedure

A mixture of ethyl 4-((N,N-diethylsulfamoyl)methyl)-2-ethylcyclopentanecarboxylate (0.570 g, 1.784 mmol) in NaOH (1 N aqueous, 10 mL, 10 mmol) was stirred at ambient temperature for about 72 h. The mixture was partitioned with DCM (10 mL). The aqueous phase was acidified to about pH=4 by addition of 6 N aqueous HCl. The solution was partitioned with DCM (10 mL). The aqueous phase was washed with DCM (2×10 mL). The organic layers were combined, dried over anhydrous MgSO4, and concd under reduced pressure to give 4-((N,N-diethylsulfamoyl)methyl)-2-ethylcyclopentanecarboxylic acid (0.375 g, 72%) as yellow oil: LC/MS (Table 1, Method b) Rt=1.95 min; MS m/z: 292 (M+H)+.

Workup

  1. customThe mixture was partitioned with DCM (10 mL)
  2. additionThe aqueous phase was acidified to about pH=4 by addition of 6 N aqueous HCl
  3. customThe solution was partitioned with DCM (10 mL)
  4. washThe aqueous phase was washed with DCM (2×10 mL)
  5. dry with materialdried over anhydrous MgSO4, and concd under reduced pressure

Sources & evidence

ORD record
ord-507c97f28ee24824ba88e1ce3a92ecbd
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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