Trifluoroacetic acid → HCID 57826661, compound

HRID 2392291Notes

Reaction equation

HRID 2392291 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-8a695889b58943308beaa5bf996d4841
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

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