Methanol → 2-[[3,5-bis(trifluoromethyl)benzoyl]amino]-4-[3-[(E)-[4-(trifluoromethyl)phenyl]methylideneamino]oxypropoxy]benzoic acid

HRID 29684Notes

Reaction equation

HRID 29684 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]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)=[CH:6][C:5]=1[NH:27][C:28](=[O:43])[C:29]1[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[C:31]([C:39]([F:42])([F:41])[F:40])[CH:30]=1.CO.[OH-].[Li+]>O1CCCC1>[F:36][C:35]([F:37])([F:38])[C:33]1[CH:34]=[C:29]([CH:30]=[C:31]([C:39]([F:41])([F:40])[F:42])[CH:32]=1)[C:28]([NH:27][C:5]1[CH:6]=[C:7]([O:10][CH2:11][CH2:12][CH2:13][O:14]/[N:15]=[CH:16]/[C:17]2[CH:18]=[CH:19][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:21][CH:22]=2)[CH:8]=[CH:9][C:4]=1[C:3]([OH:44])=[O:2])=[O:43]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 57449660methyl 2-[[3,5-bis(trifluoromethyl)benzoyl]amino]-4-[3-[(E)-[4-(trifluoromethyl)phenyl]methylideneamino]oxypropoxy]benzoate

Product 1

HCID 112043612-[[3,5-bis(trifluoromethyl)benzoyl]amino]-4-[3-[(E)-[4-(trifluoromethyl)phenyl]methylideneamino]oxypropoxy]benzoic acidYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This compound was produced using similar methods as those used in Step 6, example 28, starting with 2-{[3,5-bis(trifluoromethyl)benzoyl]amino}-4-{3-[({(1E)-[4-(trifluoromethyl)phenyl]methylidene}amino)oxy]propoxy}benzoic acid methyl ester (0.22 g, 0.35 mmol), 1:1 methanol:tetrahydrofuran (10 mL) and 4N aqueous lithium hydroxide solution (0.26 mL). The crude material was triturated with hot hexanes and filtered. The product was then crystallized from hot chloroform (10 mL) by the addition of room temperature hexanes (100 mL), and allowing the mixture to sit for 2 hours to give 2-{[3,5-bis(trifluoromethyl)benzoyl]amino}-4-{3-[({(1E)-[4-(trifluoromethyl)phenyl]methylidene}amino)oxy]propoxy}benzoic acid (0.055 g, 26%) as a white solid. mp=218-219° C. (dec). 1H NMR (500 MHz, DMSO-d6); δ 13.50 (bs, 1H), 12.72 (s, 1H), 8.49 (s, 2H), 8.44 (s, 1H), 8.38 (s, 1H), 8.31 (d, 1H), 7.99 (d, 1H), 7.80-7.71 (AA′BB′, 4H), 6.82 (dd, 1H), 4.34 (t, 2H), 4.22 (t, 2H), 2.18 (m, 2H). Mass spec (MW 622.44); (ES+) m/z 623.05, (ES−) m/z 621.50. Elemental analysis; Calculated for C27H19F9N2O5: C, 52.10; H, 3.08; N, 4.50. Found: C, 51.78; H, 3.03; N, 4.26.

Workup

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

Sources & evidence

ORD record
ord-2872cf816a1f460f9054a3b7b350bb9d
Source dataset
uspto-grants-2008_09
Patent number
US07420083B2

Reaction notes

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