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

HRID 923534Notes

Reaction equation

HRID 923534 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][CH: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:44])([F:45])[F:43])=[CH:27][CH: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 892850004-((N-(2-(tert-butoxy)-2-oxoethyl)-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)benzamido)methyl)phenyl 4-(heptyloxy)benzoate

Product 1

HCID 714890822-(N-(4-((4-(heptyloxy)benzoyl)oxy)benzyl)-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)benzamido)acetic acidYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared using General Procedures 8: To 4-((N-(2-(tert-butoxy)-2-oxoethyl)-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)benzamido)methyl)phenyl 4-(heptyloxy)benzoate INT-6 (555 mg, 0.702 mmol) in DCM (3 mL) was added TFA (3 mL). The reaction was stirred at room temperature for 2 h then purified by chromatography (EA/hexanes+1% acetic acid) to provide 385 mg (74%) of 2-(N-(4-((4-(heptyloxy)benzoyl)oxy)benzyl)-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)benzamido)acetic acid 3. LCMS-ESI (m/z) calculated for C40H41F3N2O8: 734; no m/z observed, tR=11.42 min (Method 2). 1H NMR (400 MHz, DMSO) δ 12.83 (s, 1H), 10.35 (s, 1H), 8.14-8.01 (m, 2H), 7.65 (d, J=8.3 Hz, 2H), 7.54-7.29 (m, 5H), 7.29-7.16 (m, 4H), 7.14-7.01 (m, 2H), 4.69 (s, 1H), 4.61 (s, 1H), 4.08 (t, J=6.5 Hz, 2H), 4.00 (s, 1H), 3.94 (s, 1H), 3.86 (s, 2H), 3.83 (s, 3H), 1.81-1.68 (m, 2H), 1.48-1.22 (m, 8H), 0.92-0.81 (t, J=6.8 Hz, 3H).

Workup

  1. customPrepared
  2. customthen purified by chromatography (EA/hexanes+1% acetic acid)

Sources & evidence

ORD record
ord-1f1f42a787d14484ad444fa28f8c761d
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

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