Trifluoroacetic acid → 2-(N-(4-((4-(heptyloxy)benzoyl)oxy)benzyl)-5-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)picolinamido)acetic acid

HRID 923556Notes

Reaction equation

HRID 923556 reaction equation
[CH2:1]([O:8][C:9]1[CH:57]=[CH:56][C:12]([C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][N:23]([CH2:48][C:49]([O:51]C(C)(C)C)=[O:50])[C:24](=[O:47])[C:25]3[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:46])[CH2:33][C:34]4[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][C:35]=4[C:42]([F:45])([F:44])[F:43])=[CH:27][N:26]=3)=[CH:18][CH:17]=2)=[O:14])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([O:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:22][N:23]([CH2:48][C:49]([OH:51])=[O:50])[C:24](=[O:47])[C:25]3[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:46])[CH2:33][C:34]4[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][C:35]=4[C:42]([F:43])([F:44])[F:45])=[CH:27][N:26]=3)=[CH:20][CH:21]=2)=[O:14])=[CH:56][CH:57]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 1176896824-((N-(2-(tert-butoxy)-2-oxoethyl)-5-(2-(4-methoxy-2 (trifluoromethyl)phenyl)acetamido)picolinamido)methyl)phenyl 4-(heptyloxy)benzoate

Product 1

HCID 892530462-(N-(4-((4-(heptyloxy)benzoyl)oxy)benzyl)-5-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)picolinamido)acetic acidYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Prepared using General Procedure 8: To a stirred solution of 4-((N-(2-(tert-butoxy)-2-oxoethyl)-5-(2-(4-methoxy-2 (trifluoromethyl)phenyl)acetamido)picolinamido)methyl)phenyl 4-(heptyloxy)benzoate INT-16 (18 mg, 0.02 mmol) in DCM (1 mL) was added a solution of TFA (0.1 mL) and DCM (0.2 mL). The reaction mixture was stirred at room temperature for 12 h. The solvent was evaporated under high vacuum to give 12 mg (75%) of 2-(N-(4-((4-(heptyloxy)benzoyl)oxy)benzyl)-5-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)picolinamido)acetic acid 298 as a white solid. LCMS-ESI (m/z) calculated for C39H40F3N3O8: 736; no m/z observed, tR=11.36 min (Method 2). 1H NMR (400 MHz, DMSO) δ 12.65 (s, 1H), 10.60 (s, 1H), 8.72 (dd, J=11.1, 2.1 Hz, 1H), 8.19-8.09 (m, 1H), 8.09-7.97 (m, 2H), 7.71 (dd, J=28.2, 8.7 Hz, 1H), 7.43 (dd, J=16.8, 8.3 Hz, 3H), 7.27-7.15 (m, 4H), 7.10 (d, J=8.9 Hz, 2H), 4.75 (d, J=23.0 Hz, 2H), 4.30 (s, 1H), 4.08 (t, J=6.5 Hz, 2H), 3.97 (s, 1H), 3.89 (s, 2H), 3.82 (d, J=2.0 Hz, 3H), 1.73 (dd, J=14.5, 6.6 Hz, 2H), 1.50-1.15 (m, 8H), 0.87 (t, J=6.9 Hz, 3H).

Workup

  1. customPrepared
  2. customThe solvent was evaporated under high vacuum

Sources & evidence

ORD record
ord-a7db9df29a0f440c9e7c07572e20ac6c
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

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