Potassium Hydroxide → 4-[3-[(E)-(4-tert-butylphenyl)methylideneamino]oxypropoxy]-2-[(4-phenylbenzoyl)amino]benzoic acid

HRID 29696Notes

Reaction equation

HRID 29696 reaction equation
C[O:2][C:3](=[O:42])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][O:14]/[N:15]=[CH:16]/[C:17]2[CH:22]=[CH:21][C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:19][CH:18]=2)=[CH:6][C:5]=1[NH:27][C:28]([C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:32][CH:31]=1)=[O:29].[OH-].[K+]>C1COCC1.CO>[C:33]1([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:34]=[CH:35][C:30]([C:28]([NH:27][C:5]2[CH:6]=[C:7]([O:10][CH2:11][CH2:12][CH2:13][O:14]/[N:15]=[CH:16]/[C:17]3[CH:18]=[CH:19][C:20]([C:23]([CH3:26])([CH3:24])[CH3:25])=[CH:21][CH:22]=3)[CH:8]=[CH:9][C:4]=2[C:3]([OH:42])=[O:2])=[O:29])=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 87734645methyl 4-[3-[(E)-(4-tert-butylphenyl)methylideneamino]oxypropoxy]-2-[(4-phenylbenzoyl)amino]benzoate

Product 1

HCID 117861574-[3-[(E)-(4-tert-butylphenyl)methylideneamino]oxypropoxy]-2-[(4-phenylbenzoyl)amino]benzoic acidYield 63,616.102%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

The desired product was prepared using a procedure similar to Step 7 of example 34. Thus, 2-[(1,1′-biphenyl-4-ylcarbonyl)amino]4-[3-({[(1E)-(4-tert-butylphenyl)methylidene]amino}oxy)propoxy]benzoic acid methyl ester (0.253 g, 0.448 mmol) was reacted with 1N KOH (0.90 ml) in THF/MeOH (6 ml/4 ml) to give 2-[(1,1′-biphenyl-4-ylcarbonyl)amino]-4-[3-({[(1E)-(4-tert-butylphenyl)methylidene]amino}oxy)propoxy]benzoic acid (0.157 g, 0.285 mol, 64%) as a white solid, mp 155-158.5° C. 1H NMR (DMSO-d6) δ 1.25 (s, 9H), 2.14-2.18 (m, 2H), 4.21 (t, J=6.3 Hz, 2H), 4.28 (t, J=6.3 Hz, 2H), 6.78 (dd, J=2.4, 8.9 Hz, 1H), 7.38-7.45 (m, 3H), 7.49-7.54 (m, 4H), 7.77 (d, J=8.3 Hz, 2H), 7.90 (d, J=8.2 Hz, 2H), 7.98-8.06 (m, 3H), 8.22 (s, 1H), 8.46 (d, 2.4 Hz, 1H) 12.60 (s, 1H); IR (solid) 3120, 2960, 1620, 1580, 1220 and 1140 cm−1; [ES(+)], m/z 551 (M+H)+; Anal. Calcd. for C34H34N2O5: C, 74.16; H, 6.22; N, 5.09, Found: C, 73.94; H, 5.91; N, 4.93.

Workup

  1. customThe desired product was prepared

Sources & evidence

ORD record
ord-cc63f4ac38cd42d89ac37b488acbd349
Source dataset
uspto-grants-2008_09
Patent number
US07420083B2

Reaction notes

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