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

HRID 923532Notes

Reaction equation

HRID 923532 reaction equation
[CH2:1]([O:8][C:9]1[CH:53]=[CH:52][C:12]([C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][N:23]([CH2:44][C:45]([O:47]C(C)(C)C)=[O:46])[C:24](=[O:43])[C:25]3[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:42])[CH2:33][C:34]4[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=4)=[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>>[CH2:1]([O:8][C:9]1[CH:53]=[CH:52][C:12]([C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][N:23]([CH2:44][C:45]([OH:47])=[O:46])[C:24](=[O:43])[C:25]3[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:42])[CH2:33][C:34]4[CH:35]=[CH:36][C:37]([O:40][CH3:41])=[CH:38][CH:39]=4)=[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]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 892531624-((N-(2-(tert-butoxy)-2-oxoethyl)-4-(2-(4-methoxyphenyl)acetamido)benzamido)methyl)phenyl 4-(heptyloxy)benzoate

Product 1

HCID 714890832-(N-(4-((4-(heptyloxy)benzoyl)oxy)benzyl)-4-(2-(4-methoxyphenyl)acetamido)benzamido)acetic acidYield 23%

Procedure

Prepared using General Procedure 8: To crude 4-((N-(2-(tert-butoxy)-2-oxoethyl)-4-(2-(4-methoxyphenyl)acetamido)benzamido)methyl)phenyl 4-(heptyloxy)benzoate INT-5 (70 mg) was added TFA (1 mL). After stirring for 1 h, the solvent was concentrated and the product was purified by preparative HPLC to provide 19 mg (23%) of 2-(N-(4-((4-(heptyloxy)benzoyl)oxy)benzyl)-4-(2-(4-methoxyphenyl)acetamido)benzamido)acetic acid 1. LCMS-ESI (m/z) calculated for C39H42N2O8: 667; found 666 [M−H]−, tR=9.51 min (Method 4). 1H NMR (400 MHz, DMSO) δ 12.80 (s, 1H), 10.31 (s, 1H), 8.16-7.97 (m, 2H), 7.69-7.58 (d, J=8.5 Hz, 2H), 7.48-7.27 (m, 4H), 7.28-7.19 (d, J=8.1 Hz, 4H), 7.15-7.05 (m, 2H), 6.93-6.82 (d, J=8.1 Hz, 2H), 4.74-4.51 (d, J=35.4 Hz, 2H), 4.15-3.80 (m, 4H), 3.71 (s, 3H), 3.66 (s, 2H), 1.84-1.66 (m, 2H), 1.48-1.19 (m, 8H), 0.93-0.80 (t, J=6.6 Hz, 3H).

Workup

  1. customPrepared
  2. concentrationthe solvent was concentrated
  3. customthe product was purified by preparative HPLC

Sources & evidence

ORD record
ord-657a492ab0e34e7aa266c4333e5c35a0
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

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