Trifluoroacetic acid → HCID 178525467, compound

HRID 1035710Notes

Reaction equation

HRID 1035710 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](/[CH:28]=[CH: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](/[CH:28]=[CH: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 178451018HCID 178451018, compound

Product 1

HCID 178525467HCID 178525467, compoundYield 25.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

35 mg of tert-butyl trans-(E)-3-{4-[4-(5-benzyl[1.3.4]thiadiazol-2-ylcarbamoyl)phenyl]-cyclohexyl}acrylate (0.07 mmol, 1 eq.) are placed in 1 mL of dichloromethane. 0.5 mL of trifluoroacetic acid (6.73 mmol, 97 eq.) is added and the reaction medium is stirred for 3 hours at room temperature. The solvent is evaporated off. The resin is triturated in ethyl acetate to give 8 mg of trans-(E)-3-{4-[4-(5-benzyl[1.3.4]thiadiazol-2-ylcarbamoyl)-phenyl]cyclohexyl}acrylic acid.

Workup

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

Sources & evidence

ORD record
ord-bd68306b85e74b90b83a5b252d02b671
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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