Hydrochloric Acid → HCID 66703598, compound

HRID 425979Notes

Reaction equation

HRID 425979 reaction equation
[OH-:1].[K+].[CH2:3]([O:10][C@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]1[NH:17][C:18]1[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:19]=1[C:20]#N)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl.C(O)C.[OH2:34]>>[CH2:3]([O:10][C@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]1[NH:17][C:18]1[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:19]=1[C:20]([OH:34])=[O:1])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 19096565Water ethanolHCID 66703713HCID 66703713, compound

Product 1

HCID 66703598HCID 66703598, compound

Conditions

Temperature
100 °C

Procedure

Potassium hydroxide aqueous solution was added to an ethanol-water mixed solution of 2-{[(1S,2S)-2-(benzyloxy)cyclohexyl]amino}-4-(trifluoromethyl)benzonitrile. This was stirred at 100° C. for 5 hours and then spontaneously cooled. After neutralizing with 1 M hydrochloric acid, the organic layer was extracted with chloroform. By concentrating the organic layer under a reduced pressure, 2-{[(1S,2S)-2-(benzyloxy)cyclohexyl]amino}-4-(trifluoromethyl)benzoic acid was obtained.

Workup

  1. temperaturespontaneously cooled
  2. extractionthe organic layer was extracted with chloroform
  3. concentrationBy concentrating the organic layer under a reduced pressure

Sources & evidence

ORD record
ord-3a731ed4a9934ff7860953b2d95370a5
Source dataset
uspto-grants-2012_01
Patent number
US08106190B2

Reaction notes

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