Trifluoroacetic acid → HCID 57513706, compound

HRID 2368419Notes

Reaction equation

HRID 2368419 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[S:19][C:18]([NH:20][C:21](=[O:35])[C:22]([NH:25][C:26](=[O:34])[C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)([CH3:24])[CH3:23])=[N:17][C:16]=2[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[F:33][C:30]1[CH:29]=[CH:28][C:27]([C:26]([NH:25][C:22]([CH3:24])([C:21](=[O:35])[NH:20][C:18]2[S:19][C:15]([CH2:14][N:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[C:16]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[N:17]=2)[CH3:23])=[O:34])=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57513831HCID 57513831, compound

Product 1

HCID 57513706HCID 57513706, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-{2-[2-(4-Fluoro-benzoylamino)-2-methyl-propionylamino]-4-phenyl-thiazol-5-ylmethyl}-piperazine-1-carboxylic acid tert-butyl ester (70 mg) and TFA (1.5 mL) in dichloromethane (3 mL) was stirred at RT for 2 h and concentrated. The residue was partitioned between dichloromethane and aq. K2CO3. The organic extract was dried over MgSO4, concentrated and purified by HPLC to give the title compound. m/z 482.2 (MH+). 1H NMR (CD3OD) 7.98-7.96 (m, 2H), 7.57 (d, J=8 Hz, 2H), 7.41 (t, J=8 Hz, 2H), 7.35 (d, J=8 Hz, 2H), 7.21 (t, J=8 Hz, 2H), 3.75 (s, 2H), 2.88-2.85 (m, 4H), 2.55-2.45 (m, 4H).

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between dichloromethane and aq. K2CO3
  3. extractionThe organic extract
  4. dry with materialwas dried over MgSO4
  5. concentrationconcentrated
  6. custompurified by HPLC

Sources & evidence

ORD record
ord-716717fffb77466495a416972f926ade
Source dataset
uspto-grants-2014_04
Patent number
US08703761B2

Reaction notes

Loading…