Trifluoroacetic acid → HCID 178526000, compound

HRID 1035725Notes

Reaction equation

HRID 1035725 reaction equation
[CH2:1]([C:8]1[S:12][C:11]([NH:13][C:14]([C:16]2[CH:21]=[CH:20][C:19]([C@H:22]3[CH2:27][CH2:26][C@H:25]([O:28][CH2:29][C:30]([O:32]C(C)(C)C)=[O:31])[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]([C@H:22]3[CH2:27][CH2:26][C@H:25]([O:28][CH2:29][C:30]([OH:32])=[O:31])[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 178451366HCID 178451366, compound

Product 1

HCID 178526000HCID 178526000, compoundYield 18.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

90 mg of tert-butyl trans-{4-[4-(5-benzyl[1.3.4]thiadiazol-2-ylcarbamoyl)phenyl]cyclohexyloxy}acetate (0.18 mmol, 1 eq.) are placed in 1 mL of dichloromethane. 0.13 mL of trifluoroacetic acid (1.77 mmol, 10 eq.) is added and the reaction medium is stirred for 18 hours at room temperature. The solvent is evaporated off. The residue is triturated in ethyl acetate and methanol to give 15 mg of trans-{4-[4-(5-benzyl[1.3.4]thiadiazol-2-ylcarbamoyl)phenyl]cyclohexyloxy}acetic acid.

Workup

  1. customThe solvent is evaporated off
  2. customThe residue is triturated in ethyl acetate

Sources & evidence

ORD record
ord-9c7d064a0b044612baf65bf24595361a
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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