Methyl 1-aminocyclohexanoate → Methyl 1-(3-((s)-1-tert-butoxycarbonyl-3-methylbutyl)ureido)cyclohexanecarboxylate

HRID 2184994Notes

Reaction equation

HRID 2184994 reaction equation
[NH2:1][C:2]1([C:8]([O:10][CH3:11])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[N-:12]=[C:13]=[O:14].[C:15]([O:19][C:20](=[O:27])[C@H:21]([CH2:23][CH:24]([CH3:26])[CH3:25])N)([CH3:18])([CH3:17])[CH3:16]>CN(C=O)C>[C:15]([O:19][C:20]([C@@H:21]([NH:12][C:13](=[O:14])[NH:1][C:2]1([C:8]([O:10][CH3:11])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1)[CH2:23][CH:24]([CH3:26])[CH3:25])=[O:27])([CH3:18])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 4048819Methyl 1-aminocyclohexanoateHCID 86588629L-leucine tert-butyl ester isocyanate

Product 1

HCID 15895596Methyl 1-(3-((s)-1-tert-butoxycarbonyl-3-methylbutyl)ureido)cyclohexanecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 28 g (179 mmol) of methyl 1-aminocyclohexane-1-carboxylate was added to a solution of 38 g (179 mmol) of L-leucine tert-butyl ester isocyanate (prepared analogously to J. S. Nowick et al., J. Org. Chem. 1996, 61, 3929) in 300 ml of absolute DMF. After stirring at room temperature for 2 hours, the reaction mixture was allowed to stand overnight. The solvent was removed in vacuo, the residue was treated with heptane and the mixture was stirred at room temperature for 2 hours. The precipitate was filtered off with suction and washed with heptane. Yield: 45.94 g (69%).

Workup

  1. customprepared analogously to J
  2. waitto stand overnight
  3. customThe solvent was removed in vacuo
  4. additionthe residue was treated with heptane
  5. stirringthe mixture was stirred at room temperature for 2 hours
  6. filtrationThe precipitate was filtered off with suction
  7. washwashed with heptane

Sources & evidence

ORD record
ord-5aefbe4dc3df4d3ab61772b13642cdd0
Source dataset
uspto-grants-2002_06
Patent number
US06399643B1

Reaction notes

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