Sodium Hydroxide → (1S,2R,4S)-4-acetamido-2-ethylcyclopentanecarboxylic acid

HRID 1969758Notes

Reaction equation

HRID 1969758 reaction equation
[C:1]([NH:4][C@@H:5]1[CH2:9][C@H:8]([C:10]([O:12]CC)=[O:11])[C@H:7]([CH2:15][CH3:16])[CH2:6]1)(=[O:3])[CH3:2].[OH-].[Na+]>Cl>[C:1]([NH:4][C@@H:5]1[CH2:9][C@H:8]([C:10]([OH:12])=[O:11])[C@H:7]([CH2:15][CH3:16])[CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58557255(1S,2R,4S)-ethyl 4-acetamido-2-ethylcyclopentanecarboxylate

Product 1

HCID 58557127(1S,2R,4S)-4-acetamido-2-ethylcyclopentanecarboxylic acidYield 88%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a flask containing (1S,2R,4S)-ethyl 4-acetamido-2-ethylcyclopentanecarboxylate (9.44 g, 41.5 mmol) was added NaOH (2 N aqueous, 141 mL, 282 mmol). After stirring at ambient temperature for about 12 h, the reaction was acidified to about pH 1 by the addition of 6 N aqueous HCl (50 mL) and extracted with EtOAc (3×500 mL). The combined organic layers were washed with brine (100 mL), dried over anhydrous MgSO4, filtered, and concd under reduced pressure to give crude (1S,2R,4S)-4-acetamido-2-ethylcyclopentanecarboxylic acid (7.25 g, 88%): LC/MS (Table 1, Method a) Rt=1.51 min; MS m/z: 200 (M−H)+.

Workup

  1. extractionextracted with EtOAc (3×500 mL)
  2. washThe combined organic layers were washed with brine (100 mL)
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered

Sources & evidence

ORD record
ord-1d18bf00de1e42aea8b3514b1a9c56bd
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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