Trifluoroacetic acid → HCID 57826661, compound

HRID 1845694Notes

Reaction equation

HRID 1845694 reaction equation
C(O)(C(F)(F)F)=O.CC([N:12]([CH2:16][C@@H:17]([NH:25][C:26]([C:28]1[S:29][CH:30]=[C:31]([C:33]2[N:37]([CH3:38])[N:36]=[CH:35][N:34]=2)[CH:32]=1)=[O:27])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)C(=O)[O-])(C)C>C(Cl)Cl>[NH2:12][CH2:16][C@@H:17]([NH:25][C:26]([C:28]1[S:29][CH:30]=[C:31]([C:33]2[N:37]([CH3:38])[N:36]=[CH:35][N:34]=2)[CH:32]=1)=[O:27])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86633572HCID 86633572, compound

Product 1

HCID 57826661HCID 57826661, compoundYield 116.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1 ml) was added to a solution of 1,1-dimethylethyl[(2S)-2-({[4-(1-methyl-1H-1,2,4-triazol-5-yl)-2-thienyl]carbonyl}amino)-3-phenylpropyl]carbamate (100 mg, 0.226 mmol) in DCM (5 ml). The reaction was stirred at RT for 30 min. The solvent was removed and the residue was purified by reverse phase HPLC (10% org ˜60% org) to give the title compound as a white solid (90 mg, 87%). LC-MS (ES) m/z 342.2 (M+H)+, 1H NMR (d4-MeOH, 400 MHz) δ 8.23 (s, 1H), 8.03 (m, 2H), 7.22-7.31 (m, 5H), 4.60 (m, 1H), 4.08 (s, 3H), 3.10-3.20 (m, 2H), 3.00 (m, 2H).

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by reverse phase HPLC (10% org ˜60% org)

Sources & evidence

ORD record
ord-9409882dda694fa486737af03a0ca637
Source dataset
uspto-grants-2015_02
Patent number
US08946278B2

Reaction notes

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