Ammonia → (1R,2R)-2-Carbamoyl-cyclohexanecarboxylic acid

HRID 1456357Notes

Reaction equation

HRID 1456357 reaction equation
[C@@H:1]12[C:10](=[O:11])[O:9][C:7](=[O:8])[C@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6]2.Cl.[NH3:13]>>[C:10]([C@@H:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C@H:2]1[C:7]([OH:9])=[O:8])(=[O:11])[NH2:13]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 12261141(-)-trans-1,2-Cyclohexanedicarboxylic Anhydride

Product 1

HCID 6928785(1R,2R)-2-Carbamoyl-cyclohexanecarboxylic acid

Procedure

To 40 ml of aqueous conc. ammonia were added 10.0 g of trans-1,2-cyclohexanedicarboxylic acid anhydride with stirring at room temperature, and the mixture was stirred at room temperature for 4 hours and 15 minutes. The pH of the reaction mixture was adjusted to 1 with conc. hydrochloric acid with stirring under ice-cooling and the precipitated crystalline solid was collected by filtration and washed with water. The crystalline solid was recrystallized from ethanol to obtain 6.93 g of the desired compound as a colorless crystalline solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 4 hours and 15 minutes
  2. stirringwith stirring under ice-
  3. temperaturecooling
  4. filtrationthe precipitated crystalline solid was collected by filtration
  5. washwashed with water
  6. customThe crystalline solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-844eed50ddaf4eb095befc98f9853d1f
Source dataset
uspto-grants-1998_12
Patent number
US05843973

Reaction notes

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