Trifluoroacetic acid → (4-{4-[5-(4-Fluorobenzyl)[1.3.4]thiadiazol-2-ylcarbamoyl]phenyl}cyclohexyl)acetic acid

HRID 1035693Notes

Reaction equation

HRID 1035693 reaction equation
[F:1][C:2]1[CH:36]=[CH:35][C:5]([CH2:6][C:7]2[S:11][C:10]([NH:12][C:13]([C:15]3[CH:20]=[CH:19][C:18]([CH:21]4[CH2:26][CH2:25][CH:24]([CH2:27][C:28]([O:30]C(C)(C)C)=[O:29])[CH2:23][CH2:22]4)=[CH:17][CH:16]=3)=[O:14])=[N:9][N:8]=2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[CH:36]=[CH:35][C:5]([CH2:6][C:7]2[S:11][C:10]([NH:12][C:13]([C:15]3[CH:20]=[CH:19][C:18]([CH:21]4[CH2:22][CH2:23][CH:24]([CH2:27][C:28]([OH:30])=[O:29])[CH2:25][CH2:26]4)=[CH:17][CH:16]=3)=[O:14])=[N:9][N:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86662111Tert-butyl (4-{4-[5-(4-fluorobenzyl)[1.3.4]thiadiazol-2-ylcarbamoyl]phenyl}cyclohexyl)acetate

Product 1

HCID 46843707(4-{4-[5-(4-Fluorobenzyl)[1.3.4]thiadiazol-2-ylcarbamoyl]phenyl}cyclohexyl)acetic acidYield 37.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.35 g of tert-butyl (4-{4-[5-(4-fluorobenzyl)[1.3.4]thiadiazol-2-ylcarbamoyl]phenyl}cyclohexyl)acetate (0.69 mmol, 1 eq.) is placed in 5 mL of dichloromethane. 1 mL of trifluoroacetic acid (13.46 mmol, 19.6 eq.) is added and the reaction medium is stirred for 18 hours at room temperature. The solvent is evaporated off and the residue is taken up in ethyl acetate, ethanol and methanol to give 117 mg of (4-{4-[5-(4-fluorobenzyl)[1.3.4]thiadiazol-2-ylcarbamoyl]phenyl}cyclohexyl)acetic acid.

Workup

  1. customThe solvent is evaporated off

Sources & evidence

ORD record
ord-37fe35f0c1614f11a1001813a68abd40
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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