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Methanol → 4-[3-[(E)-(4-phenylphenyl)methylideneamino]oxypropoxy]-2-[[4-(trifluoromethoxy)benzoyl]amino]benzoic acid

HRID 29678
Notes
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Reaction equation

HRID 29678 reaction equation
C[O:2][C:3](=[O:43])[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]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:19][CH:18]=2)=[CH:6][C:5]=1[NH:29][C:30](=[O:42])[C:31]1[CH:36]=[CH:35][C:34]([O:37][C:38]([F:41])([F:40])[F:39])=[CH:33][CH:32]=1.CO.[OH-].[Li+]>O1CCCC1>[C:20]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:19]=[CH:18][C:17](/[CH:16]=[N:15]/[O:14][CH2:13][CH2:12][CH2:11][O:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:43])=[O:2])=[C:5]([NH:29][C:30](=[O:42])[C:31]3[CH:36]=[CH:35][C:34]([O:37][C:38]([F:40])([F:41])[F:39])=[CH:33][CH:32]=3)[CH:6]=2)=[CH:22][CH:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 87735102methyl 4-[3-[(E)-(4-phenylphenyl)methylideneamino]oxypropoxy]-2-[[4-(trifluoromethoxy)benzoyl]amino]benzoate

Product 1

HCID 114218374-[3-[(E)-(4-phenylphenyl)methylideneamino]oxypropoxy]-2-[[4-(trifluoromethoxy)benzoyl]amino]benzoic acidYield 96.4%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

This compound was produced using similar methods as those used in Step 6, example 28, starting with 4-[3-({[(1E)-1,1′-biphenyl-4-ylmethylidene]amino}oxy)propoxy]-2-{[4-(trifluoromethoxy)benzoyl]amino}benzoic acid methyl ester (0.31 g, 0.52 mmol), 1:1 methanol:tetrahydrofuran (10 mL) and 4N aqueous lithium hydroxide solution (0.39 mL). The crude material was crystallized from hot chloroform (10 mL) by the addition of room temperature hexanes (100 mL), and allowing the mixture to sit for 2 hours. The product was isolated and then triturated with hexanes to give 4-[3-({[(1E)-1,1′-biphenyl-4-ylmethylidene]amino}oxy)propoxy]-2-{[4-(trifluoromethoxy)benzoyl]amino}benzoic acid (0.29 g, 95%) as a white solid. mp=194.5-195.5° C. 1H NMR (500 MHz, DMSO-d6); δ 13.49 (bs, 1H), 12.46 (s, 1H), 8.40 (s, 1H), 8.31 (s, 1H), 8.05 (d, 2H), 8.00 (d, 1H), 7.70-7.66 (m, 6H), 7.58 (d, 2H), 7.46 (t, 2H), 7.37(t, 1H), 6.81 (d, 1H), 4.31 (t, 2H), 4.22 (t, 2H), 2.18 (m, 2H). Mass spec (MW 578.54); (ES+) m/z 577.43 Elemental analysis; Calculated for C31H25F3N2O6: C, 64.36; H, 4.36; N, 4.84. Found: C, 63.78; H, 4.18; N, 4.77.

Workup

  1. customThis compound was produced
  2. customThe crude material was crystallized from hot chloroform (10 mL) by the addition of room temperature hexanes (100 mL)
  3. customThe product was isolated
  4. customtriturated with hexanes

Sources & evidence

ORD record
ord-f50fb79c548e4caba5fa44954f53e739
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07420083B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes