Trifluoroacetic acid → HCID 67497136, compound

HRID 1628196Notes

Reaction equation

HRID 1628196 reaction equation
[O:1]=[C:2]([NH:19][C:20]1[S:21][C:22]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)=[N:23][N:24]=1)[C@@H:3]([NH:11]C(=O)OC(C)(C)C)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:11][C@@H:3]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:2]([NH:19][C:20]1[S:21][C:22]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)=[N:23][N:24]=1)=[O:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67496740HCID 67496740, compound

Product 1

HCID 67497136HCID 67497136, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a solution of (S)-tert-butyl 1-oxo-3-phenyl-1-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-ylamino)propan-2-ylcarbamate (0.426 g, 1.00 mmol) in CH2Cl2 (5.0 mL) was injected trifluoroacetic acid (7.44 ml, 100 mmol) and let stir for 3 h. Reaction stripped of solvent. The residue was purified by silica gel flash chromatography (0-10% MeOH/CH2Cl2) to afford (S)-2-amino-3-phenyl-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)propanamide (0.306 g. 93.9% yield)

Workup

  1. customReaction
  2. customThe residue was purified by silica gel flash chromatography (0-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-57143bbc16d44e55a3ce35806092c5dc
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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