Citric Acid → 4-Tert-butoxycarbonylamino-4-cyclohexyl-butyric acid

HRID 491871Notes

Reaction equation

HRID 491871 reaction equation
C[O:2][C:3](=[O:21])[CH2:4][CH2:5][CH:6]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[C:17]([O:16][C:14]([NH:13][CH:6]([CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1)[CH2:5][CH2:4][C:3]([OH:21])=[O:2])=[O:15])([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 670235234-Tert-butoxycarbonylamino-4-cyclohexyl-butyric acid methyl ester

Product 1

HCID 670235684-Tert-butoxycarbonylamino-4-cyclohexyl-butyric acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-tert-butoxycarbonylamino-4-cyclohexyl-butyric acid methyl ester (9 g) in MeOH (100 mL) was added 1N NaOH (31 mL) and the reaction mixture was stirred at room temperature overnight. Citric acid (7 g) was then added, and the MeOH was removed under vacuum. The product was extracted with EtOAc (300 mL). The organic layer was washed with aqueous NaCl solution, dried with MgSO4, and evaporated to yield 4-tert-butoxycarbonylamino-4-cyclohexyl-butyric acid as an off white solid.

Workup

  1. customthe MeOH was removed under vacuum
  2. extractionThe product was extracted with EtOAc (300 mL)
  3. washThe organic layer was washed with aqueous NaCl solution
  4. dry with materialdried with MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-d671e0b59aa54f6caa12e46fe0741f0f
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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