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

HRID 29694Notes

Reaction equation

HRID 29694 reaction equation
C[O:2][C:3](=[O:44])[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](=[O:43])/[CH:29]=[CH:30]/[C:31]1[CH:36]=[CH:35][C:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:33][CH:32]=1.[OH-].[K+]>C1COCC1.CO>[C:34]1([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:33]=[CH:32][C:31](/[CH:30]=[CH:29]/[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])([CH3:25])[CH3:24])=[CH:21][CH:22]=3)[CH:8]=[CH:9][C:4]=2[C:3]([OH:44])=[O:2])=[O:43])=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 87734082methyl 4-[3-[(E)-(4-tert-butylphenyl)methylideneamino]oxypropoxy]-2-[[(E)-3-(4-phenylphenyl)prop-2-enoyl]amino]benzoate

Product 1

HCID 112845964-[3-[(E)-(4-tert-butylphenyl)methylideneamino]oxypropoxy]-2-[[(E)-3-(4-phenylphenyl)prop-2-enoyl]amino]benzoic acidYield 68.5%

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-{[(2E)-3-(1,1′-biphenyl-4-yl)prop-2-enoyl]amino}4-[3-({[(1E)-(4-tert-butylphenyl)methylidene]amino}oxy)propoxy]benzoic acid methyl ester (0.148 g, 0.251 mmol) was reacted with 1N KOH (0.50 ml) in THF/MeOH (6 ml/4 ml) to give 2-{[(2E)-3-(1,1′-biphenyl-4-yl)prop-2-enoyl]amino}-4-[3-({[(1E)-(4-tert-butylphenyl)methylidene]amino}oxy)propoxy]benzoic acid (0.099 g, 0.172 mmol, 68%) as a white solid, mp 169-171° C. 1H NMR (DMSO-d6) δ 1.26 (s, 9H), 2.13-2.17 (m, 2H), 4.18 (t, J=6.4 Hz, 2H), 4.27 (t, J=6.3 Hz, 2H), 6.75 (dd, J=2.6, 8.9 Hz, 1H), 6.89 (d, J=15.6 Hz, 1H), 7.38-7.43 (m, 3H), 7.46-7.54 (m, 4H), 7.67 (d, J=15.6 Hz, 1H), 7.70-7.76 (m, 4H), 7.83 (d, J=8.2 Hz, 2H), 7.96 (d, J=8.9 Hz, 1H), 8.23 (s, 1H), 8.38 (d, J=2.4 Hz, 1H), 11.75 (s, 1H), 13.3 (s, 1H); IR (solid) 2960, 1680, 1610, 1580, 1540 and 1200 cm−1; [ES(−)], m/z 575 (M−H)−; Anal. Calcd. for C36H36N2O5: C, 74.98; H, 6.29; N, 4.86, Found: C, 74.57; H, 6.32; N, 4.89.

Workup

  1. customThe desired product was prepared

Sources & evidence

ORD record
ord-ac665fb38a944750a7e63fe5bb20fb80
Source dataset
uspto-grants-2008_09
Patent number
US07420083B2

Reaction notes

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