Hydrochloric Acid → 4-(Cyclopropanesulfonamido)-2-methylcyclopentanecarboxylic acid

HRID 2204571Notes

Reaction equation

HRID 2204571 reaction equation
[CH:1]1([S:4]([NH:7][CH:8]2[CH2:12][CH:11]([C:13]([O:15]CC)=[O:14])[CH:10]([CH3:18])[CH2:9]2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[OH-].[Na+].Cl>>[CH:1]1([S:4]([NH:7][CH:8]2[CH2:12][CH:11]([C:13]([OH:15])=[O:14])[CH:10]([CH3:18])[CH2:9]2)(=[O:6])=[O:5])[CH2:2][CH2:3]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58009782Ethyl 4-(cyclopropanesulfonamido)-2-methylcyclopentanecarboxylate

Product 1

HCID 580099884-(Cyclopropanesulfonamido)-2-methylcyclopentanecarboxylic acid

Procedure

To a flask containing ethyl 4-(cyclopropanesulfonamido)-2-methylcyclopentanecarboxylate (7.5 g, 27.3 mmol) was added aqueous NaOH (1N, 150 mL, 150 mmol). After stirring at ambient temperature for about 5 h, the reaction was acidified to about pH 1 with aqueous 6 N HCl and extracted with DCM (3×100 mL). The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure to give crude 4-(cyclopropanesulfonamido)-2-methylcyclopentanecarboxylic acid containing about 5 mol % DCM (6.6 g, 97%) as a white solid: 1H NMR (DMSO-d6) δ 12.09 (s, 1H), 7.11 (d, J=8.1 Hz, 1H), 3.66-3.53 (m, 1H), 2.78-2.68 (m, 1H), 2.50 (tq, J=5.1, 7.7 Hz, 1H), 2.29-2.17 (m, 1H), 2.17-2.01 (m, 2H), 1.82 (dt, J=9.9, 12.7 Hz, 1H), 1.24 (dt, J=8.9, 12.4 Hz, 1H), 0.98-0.85 (m, 7H).

Workup

  1. extractionextracted with DCM (3×100 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-35e66e020f7c4cc697d936a0fe6ab531
Source dataset
uspto-grants-2016_06
Patent number
US09365579B2

Reaction notes

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