1-Aminocyclohexanecarboxylic acid → 1-(Cbz-amino)cyclohexanecarboxylic acid

HRID 276249Notes

Reaction equation

HRID 276249 reaction equation
[NH2:1][C:2]1([C:8]([OH:10])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.Cl[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]>[OH-].[Na+]>[CH2:15]([O:14][C:12]([NH:1][C:2]1([C:8]([OH:10])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1)=[O:13])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 13661-Aminocyclohexanecarboxylic acidHCID 10387Benzyl chloroformate

Product 1

HCID 113578861-(Cbz-amino)cyclohexanecarboxylic acidYield 89.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

To a solution of l-aminocyclohexane-1-carboxylic acid (10.0 g, 70.0 mmol) in a 1M NaOH solution (100 mL) was added benzyl chloroformate (12.0 ml, 84.0 mmol). The reaction mixture was stirred for 2 h while maintaining pH 9 by addition of a 1M NaOH solution as necessary. The resulting solution was washed with Et2O (2×100 mL), then the aqueous layer was adjusted to pH 0 with a conc. HCl solution and the solution was extracted with EtOAc (3×150 mL). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure to yield 1-(benzyloxycarbonylamino)cyclohexane-1-carboxylic acid (17.3 g, 89%): TLC (25% EtOAc/hex) Rf0.07.

Workup

  1. temperaturewhile maintaining pH 9
  2. washThe resulting solution was washed with Et2O (2×100 mL)
  3. extractionthe solution was extracted with EtOAc (3×150 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-96e8f18f2acb48c4a45d10eda0248a35
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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