Trifluoroacetic acid → HCID 178522636, compound

HRID 1035720Notes

Reaction equation

HRID 1035720 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:34]=[CH:35][CH:36]=1)[CH2:5][C:6]1[S:10][C:9]([NH:11][C:12]([C:14]2[CH:15]=[CH:16][C:17]([O:20][C@@H:21]3[CH2:26][CH2:25][C@H:24]([C:27]([O:29]C(C)(C)C)=[O:28])[CH2:23][CH2:22]3)=[N:18][CH:19]=2)=[O:13])=[N:8][N:7]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:34]=[CH:35][CH:36]=1)[CH2:5][C:6]1[S:10][C:9]([NH:11][C:12]([C:14]2[CH:15]=[CH:16][C:17]([O:20][C@@H:21]3[CH2:22][CH2:23][C@H:24]([C:27]([OH:29])=[O:28])[CH2:25][CH2:26]3)=[N:18][CH:19]=2)=[O:13])=[N:8][N:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178451167HCID 178451167, compound

Product 1

HCID 178522636HCID 178522636, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.264 g of tert-butyl cis-4-{5-[5-(3-chlorobenzyl)[1.3.4]thiadiazol-2-ylcarbamoyl]pyridin-2-yloxy}cyclohexanecarboxylate (0.5 mmol, 1 eq.) is placed in 5 mL of dichloromethane with stirring. 0.37 mL of trifluoroacetic acid (4.99 mmol, 10 eq.) is added slowly. After stirring for 18 hours at room temperature, the medium is concentrated, taken up and evaporated successively with ethanol and dichloromethane. The residue is triturated with diethyl ether, drained and filtered to give 0.213 g of cis-4-{5-[5-(3-chlorobenzyl)-[1.3.4]thiadiazol-2-ylcarbamoyl]pyridin-2-yloxy}cyclohexanecarboxylic acid.

Workup

  1. stirringAfter stirring for 18 hours at room temperature
  2. concentrationthe medium is concentrated
  3. customevaporated successively with ethanol and dichloromethane
  4. customThe residue is triturated with diethyl ether
  5. filtrationfiltered

Sources & evidence

ORD record
ord-ea1117dcfc064ba18291d29c8bc3d4cd
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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