1-Aminocyclohexanecarboxylic acid → 1-[(Methoxycarbonyl)amino]cyclohexanecarboxylic acid

HRID 2185003Notes

Reaction equation

HRID 2185003 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][CH3:15])=[O:13].[OH-].[Na+]>C1COCC1.O>[CH3:15][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]

Participants

6

Reactant 3

HCID 13661-Aminocyclohexanecarboxylic acidHCID 6586Methyl chloroformateHCID 14798Sodium Hydroxide

Product 1

HCID 116008741-[(Methoxycarbonyl)amino]cyclohexanecarboxylic acidYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 39.9 g (279 mmol) of 1-aminocyclohexane-1-carboxylic acid in a mixture of 75 ml of THF and 75 ml of water was treated dropwise with 23.8 ml of methyl chloroformate, dissolved in 40 ml of THF, such that the temperature of the suspension did not rise above 50° C. In the course of this, the pH of the solution was kept between 8.5 and 9.5 by addition of 25% strength sodium hydroxide solution. After stirring at pH 8 for 30 minutes, the mixture was diluted with water, the THF was removed in vacuo and the aqueous phase was washed twice with methyl tert-butyl ether. The aqueous phase was adjusted to pH 2 using 6 N hydrochloric acid and extracted successively with methyl tert-butyl ether and dichloromethane. The combined organic phases were concentrated in vacuo. The residue was triturated with diethyl ether and the product was filtered off. 47.85 g (85%) of 1-methoxycarbonylaminocyclohexane-1-carboxylic acid were obtained.

Workup

  1. customdid not rise above 50° C
  2. customthe THF was removed in vacuo
  3. washthe aqueous phase was washed twice with methyl tert-butyl ether
  4. extractionextracted successively with methyl tert-butyl ether and dichloromethane
  5. concentrationThe combined organic phases were concentrated in vacuo
  6. customThe residue was triturated with diethyl ether
  7. filtrationthe product was filtered off

Sources & evidence

ORD record
ord-eef5f187c73e47fea5a85b16005185fc
Source dataset
uspto-grants-2002_06
Patent number
US06399643B1

Reaction notes

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