Trifluoroacetic acid → HCID 178525545, compound

HRID 1035737Notes

Reaction equation

HRID 1035737 reaction equation
[OH:1][CH:2]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:3][CH2:4][C:5]1[S:9][C:8]([NH:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([C@H:19]3[CH2:24][CH2:23][C@H:22]([CH2:25][C:26]([O:28]C(C)(C)C)=[O:27])[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)=[O:12])=[N:7][N:6]=1.C(O)(C(F)(F)F)=O>ClCCl>[OH:1][CH:2]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:3][CH2:4][C:5]1[S:9][C:8]([NH:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([C@H:19]3[CH2:20][CH2:21][C@H:22]([CH2:25][C:26]([OH:28])=[O:27])[CH2:23][CH2:24]3)=[CH:15][CH:14]=2)=[O:12])=[N:7][N:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178451078HCID 178451078, compound

Product 1

HCID 178525545HCID 178525545, compoundYield 15.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.146 g of tert-butyl trans-(4-{4-[5-(3-hydroxy-3-phenylpropyl)[1.3.4]thiadiazol-2-ylcarbamoyl]phenyl}cyclohexyl)acetate (0.27 mmol, 1 eq.) is placed in 2 mL of dichloromethane with stirring. 0.4 mL of TFA (5.45 mmol, 20 eq.) is added. After stirring for 4 hours, the reaction medium is evaporated and the residue is chromatographed on silica gel, eluting with a gradient of methanol in dichloromethane ranging from 1% to 10%. The fractions of interest are concentrated, and triturated with ethyl acetate and methanol. 0.020 g of trans-(4-{4-[5-(3-hydroxy-3-phenylpropyl)[1.3.4]thiadiazol-2-ylcarbamoyl]phenyl}cyclohexyl)acetic acid is obtained.

Workup

  1. stirringAfter stirring for 4 hours
  2. customthe reaction medium is evaporated
  3. customthe residue is chromatographed on silica gel
  4. washeluting with a gradient of methanol in dichloromethane ranging from 1% to 10%
  5. concentrationThe fractions of interest are concentrated
  6. customtriturated with ethyl acetate and methanol

Sources & evidence

ORD record
ord-8a5c32e1f1684bb493b4ff8d3f819b18
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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