Methanol → 2-(4-(2-(2,6-dimethoxyphenyl)acetamido)-N-(4-(3-(4'-methyl-[1,1'-biphenyl]-4-yl)-1,2,4-oxadiazol-5-yl)benzyl)benzamido)acetic acid

HRID 923610Notes

Reaction equation

HRID 923610 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](OC)=[CH:5][C:4]=1[CH2:11][C:12]([NH:14][C:15]1[CH:56]=[CH:55][C:18]([C:19]([N:21]([CH2:47][C:48]([O:50]C(C)(C)C)=[O:49])[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]3[O:33][N:32]=[C:31]([C:34]4[CH:39]=[CH:38][C:37]([C:40]5[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=5)=[CH:36][CH:35]=4)[N:30]=3)=[CH:25][CH:24]=2)=[O:20])=[CH:17][CH:16]=1)=[O:13].[CH3:57][OH:58].[Li+].[OH-]>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:58][CH3:57])[C:4]=1[CH2:11][C:12]([NH:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]([N:21]([CH2:47][C:48]([OH:50])=[O:49])[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]3[O:33][N:32]=[C:31]([C:34]4[CH:35]=[CH:36][C:37]([C:40]5[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=5)=[CH:38][CH:39]=4)[N:30]=3)=[CH:25][CH:24]=2)=[O:20])=[CH:55][CH:56]=1)=[O:13]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 71111955tert-butyl 2-(4-(2-(2,5-dimethoxyphenyl)acetamido)-N-(4-(3-(4'-methyl-[1,1'-biphenyl]-4-yl)-1,2,4-oxadiazol-5-yl)benzyl)benzamido)acetate

Product 1

HCID 711116422-(4-(2-(2,6-dimethoxyphenyl)acetamido)-N-(4-(3-(4'-methyl-[1,1'-biphenyl]-4-yl)-1,2,4-oxadiazol-5-yl)benzyl)benzamido)acetic acidYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared using General Procedure 9. To a stirring solution of tert-butyl 2-(4-(2-(2,5-dimethoxyphenyl)acetamido)-N-(4-(3-(4′-methyl-[1,1′-biphenyl]-4-yl)-1,2,4-oxadiazol-5-yl)benzyl)benzamido)acetate INT-66 (45 mg, 0.060 mmol) in THF (2 mL) and MeOH (0.25 mL) was added 1 M LiOH (120 μL, 0.120 mmol). The reaction mixture was stirred at room temperature for 20 h and a precipitate was formed. The mixture was filtered under vacuum and the captured solid washed with diethyl ether (5 mL). The captured solid was dried in a vacuum oven to provide 20 mg (48%) of 2-(4-(2-(2,6-dimethoxyphenyl)acetamido)-N-(4-(3-(4′-methyl-[1,1′-biphenyl]-4-yl)-1,2,4-oxadiazol-5-yl)benzyl)benzamido)acetic acid 458. LCMS-ESI (m/z) calculated for C41H36N4O7: 696; found 697 [M+H]+, tR=9.08 min (Method 9). 1H NMR (400 MHz, DMSO) δ 9.70 (s, 1H), 8.22-8.12 (m, 4H), 7.92-7.83 (m, 2H), 7.70-7.64 (m, 2H), 7.63-7.54 (m, 4H), 7.53-7.46 (m, 2H), 7.33 (d, J=7.9 Hz, 2H), 7.22 (t, J=8.3 Hz, 1H), 6.67 (d, J=8.3 Hz, 2H), 4.80 (s, 2H), 3.78 (s, 6H), 3.67 (s, 2H), 3.47 (s, 2H), 2.39 (s, 3H).

Workup

  1. customPrepared
  2. customa precipitate was formed
  3. filtrationThe mixture was filtered under vacuum
  4. washthe captured solid washed with diethyl ether (5 mL)
  5. customThe captured solid was dried in a vacuum oven

Sources & evidence

ORD record
ord-7ad0a9b38faa47228a74152e0c167353
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

Loading…