Trifluoroacetic acid → 4-[4-(5-Benzyl[1.3.4]thiadiazol-2-ylcarbamoyl)phenyl]cyclohexanecarboxylic acid

HRID 1035735Notes

Reaction equation

HRID 1035735 reaction equation
[CH2:1]([C:8]1[S:12][C:11]([NH:13][C:14]([C:16]2[CH:21]=[CH:20][C:19]([CH:22]3[CH2:27][CH2:26][CH:25]([C:28]([O:30]C(C)(C)C)=[O:29])[CH2:24][CH2:23]3)=[CH:18][CH:17]=2)=[O:15])=[N:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([C:8]1[S:12][C:11]([NH:13][C:14]([C:16]2[CH:17]=[CH:18][C:19]([CH:22]3[CH2:27][CH2:26][CH:25]([C:28]([OH:30])=[O:29])[CH2:24][CH2:23]3)=[CH:20][CH:21]=2)=[O:15])=[N:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66739876Tert-butyl 4-[4-(5-benzyl[1.3.4]thiadiazol-2-ylcarbamoyl)phenyl]cyclohexane-carboxylate

Product 1

HCID 468516374-[4-(5-Benzyl[1.3.4]thiadiazol-2-ylcarbamoyl)phenyl]cyclohexanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

85 mg of tert-butyl 4-[4-(5-benzyl[1.3.4]thiadiazol-2-ylcarbamoyl)phenyl]cyclohexanecarboxylate (0.18 mmol, 1 eq.) are placed in 1 mL of dichloromethane. 1 mL of trifluoroacetic acid (13.46 mmol, 76 eq.) is added and the reaction medium is stirred for 3 hours at room temperature. The solvents are evaporated off and the residue is taken up in ethyl acetate and ethanol to give, after filtration, 30 mg of 4-[4-(5-benzyl[1.3.4]-thiadiazol-2-ylcarbamoyl)phenyl]cyclohexanecarboxylic acid.

Workup

  1. customThe solvents are evaporated off
  2. customethanol to give
  3. filtrationafter filtration, 30 mg of 4-[4-(5-benzyl[1.3.4]-thiadiazol-2-ylcarbamoyl)phenyl]cyclohexanecarboxylic acid

Sources & evidence

ORD record
ord-eef5b6e5a7f04deea70b5ca294aac22c
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

Loading…