Trifluoroacetic acid → HCID 178457871, compound

HRID 1257646Notes

Reaction equation

HRID 1257646 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14](=[O:19])[NH:15][CH:16]([CH3:18])[CH3:17])[CH2:10][CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:16]([NH:15][C:14]([C@H:11]1[CH2:10][CH2:9][C@H:8]([NH2:7])[CH2:13][CH2:12]1)=[O:19])([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178457874HCID 178457874, compound

Product 1

HCID 178457871HCID 178457871, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of trans (4-isopropylcarbamoyl-cyclohexyl)-carbamic acid tert-butyl ester (1.35 g, 4.75 mmoll) in DCM (25 ml) was treated with TFA (5 ml) at ambient temperature for 1 hour. The solvent was evaporated under vacuum and the residues diluted with water and extracted into ethyl acetate. The combined organic extracts were washed with 1M sodium hydroxide, water and brine, dried with magnesium sulfate and concentrated under vacuum affording 400 mg (46%) of trans 4-amino-cyclohexanecarboxylic acid isopropylamide as a white solid. LCMS (Method B, ESI): RT=0.43 min, m+H=185.21; 1H NMR (400 MHz, DMSO) δ: 7.50 (d; 1H); 3.81-3.75 (m; 1H); 2.55 (m, 1H); 1.94 (m; 1H); 1.79 (m; 2H); 1.69-1.58 (m; 2H); 1.35 (m; 2H); 1.01 (d; 6H) 0.99 (m; 2H).

Workup

  1. customThe solvent was evaporated under vacuum
  2. additionthe residues diluted with water
  3. extractionextracted into ethyl acetate
  4. washThe combined organic extracts were washed with 1M sodium hydroxide, water and brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-01b9df6e540a47d4956e84704b331637
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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