Trifluoroacetic acid → HCID 57513704, compound

HRID 2368417Notes

Reaction equation

HRID 2368417 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[S:20][C:19]([NH:21][C:22](=[O:36])[C:23]([NH:26][C:27](=[O:35])[C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)([CH3:25])[CH3:24])=[N:18][C:17]=2[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[F:34][C:31]1[CH:30]=[CH:29][C:28]([C:27]([NH:26][C:23]([CH3:25])([C:22](=[O:36])[NH:21][C:19]2[S:20][C:16]([C:14]([N:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[O:15])=[C:17]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[N:18]=2)[CH3:24])=[O:35])=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57513830HCID 57513830, compound

Product 1

HCID 57513704HCID 57513704, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-{2-[2-(4-Fluoro-benzoylamino)-2-methyl-propionylamino]-4-phenyl-thiazole-5-carbonyl}-piperazine-1-carboxylic acid tert-butyl ester (120 mg) and TFA (3 mL) in dichloromethane (3 mL) was stirred at RT for 1 h. The mixture was concentrated, and the residue was partitioned between ethyl acetate and aq. K2CO3. The organic extract was dried over MgSO4 and concentrated. The residue was taken up in dichloromethane-methanol (3:1 v/v), and 2 M HCl (in ether, 100 uL) was added. The mixture was stirred at RT for 10 min and concentrated to give hydrochloride salt of the title compound. LCMS method A, retention time 1.0 min. m/z 496.1 (M+H+).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was partitioned between ethyl acetate and aq. K2CO3
  3. extractionThe organic extract
  4. dry with materialwas dried over MgSO4
  5. concentrationconcentrated
  6. addition2 M HCl (in ether, 100 uL) was added
  7. stirringThe mixture was stirred at RT for 10 min
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f18335ea37e846338aeaf0d9f0e5a5e3
Source dataset
uspto-grants-2014_04
Patent number
US08703761B2

Reaction notes

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