Ammonia → (2R)-2-cyclohexyl-2-hydroxy-2-phenylacetamide

HRID 2383358Notes

Reaction equation

HRID 2383358 reaction equation
[CH:1]1([C@@:7]([OH:17])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8](O)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N1C=CN=C1)([N:20]1C=CN=C1)=O.N>ClCCl>[CH:1]1([C@@:7]([OH:17])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([NH2:20])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 777377Cyclohexylphenylglycolic acid, (-)-

Product 1

HCID 59145953(2R)-2-cyclohexyl-2-hydroxy-2-phenylacetamideYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2R)-2-Cyclohexyl-2-hydroxy-2-phenylacetic acid (preparation 36, 4.87 g, 20.8 mmol) was dissolved in dichloromethane (150 mL) and carbonyldiimidazole (3.37 g, 20.8 mmol) added in one portion. After stirring for 1 hour at room temperature, 0.880 ammonia (21 mL) was added and stirring continued at room temperature for 18 hours. The organic layer was separated, washed with brine (50 mL), dried over magnesium sulphate, filtered and the solvent removed in vacuo to furnish the title compound as a white foam in 92% yield, 4.56 g.

Workup

  1. stirringstirring
  2. waitcontinued at room temperature for 18 hours
  3. customThe organic layer was separated
  4. washwashed with brine (50 mL)
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-033a9e75d4ad492cb9ea556610112769
Source dataset
uspto-grants-2012_09
Patent number
US08263623B2

Reaction notes

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