Trifluoroacetic acid → 4-Amino-1-hydroxy-N-(1-phenylethyl)cyclohexanecarboxamide

HRID 1944729Notes

Reaction equation

HRID 1944729 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][CH:15]1[CH2:20][CH2:19][C:18]([OH:32])([C:21](=[O:31])[NH:22][CH:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH3:24])[CH2:17][CH2:16]1)(C)(C)C>ClCCl>[NH2:14][CH:15]1[CH2:20][CH2:19][C:18]([OH:32])([C:21]([NH:22][CH:23]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH3:24])=[O:31])[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58292016[4-Hydroxy-4-(1-phenyl-ethylcarbamoyl)-cyclohexyl]-carbamic acid tert-butyl ester

Product 1

HCID 582917954-Amino-1-hydroxy-N-(1-phenylethyl)cyclohexanecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trifluoroacetic acid (1.5 ml) was added to a solution of crude [4-hydroxy-4-(1-phenyl-ethylcarbamoyl)-cyclohexyl]-carbamic acid tert-butyl ester (320 mg) in dichloromethane (6.0 ml). The reaction was judged to be complete by LCMS in less than 90 minutes. The reaction was diluted with dichloromethane and quenched to pH 12 using 5N sodium hydroxide. The crude product was extracted with two volumes of dichloromethane, dried over sodium sulfate, filtered and concentrated to 4-amino-1-hydroxy-cyclohexanecarboxylic acid (1-phenyl-ethyl)-amide (210 mg). LCMS M+H=263.2.

Workup

  1. waitto be complete by LCMS in less than 90 minutes
  2. customquenched to pH 12
  3. extractionThe crude product was extracted with two volumes of dichloromethane
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to 4-amino-1-hydroxy-cyclohexanecarboxylic acid (1-phenyl-ethyl)-amide (210 mg)

Sources & evidence

ORD record
ord-9f294006ccf943639aea6c14656687cd
Source dataset
uspto-grants-2013_03
Patent number
US08394858B2

Reaction notes

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