Methanol → HCID 11399438, compound

HRID 29682Notes

Reaction equation

HRID 29682 reaction equation
C[O:2][C:3](=[O:46])[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:45])[C:31]1[CH:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=[C:33]([C:41]([F:44])([F:43])[F:42])[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:21]=[CH:22][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:46])=[O:2])=[C:5]([NH:29][C:30](=[O:45])[C:31]3[CH:36]=[C:35]([C:37]([F:39])([F:40])[F:38])[CH:34]=[C:33]([C:41]([F:42])([F:43])[F:44])[CH:32]=3)[CH:6]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 87734636methyl 2-[[3,5-bis(trifluoromethyl)benzoyl]amino]-4-[3-[(E)-(4-phenylphenyl)methylideneamino]oxypropoxy]benzoate

Product 1

HCID 11399438HCID 11399438, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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-{[3,5-bis(trifluoromethyl)benzoyl]amino}benzoic acid methyl ester (0.25 g, 0.39 mmol), 1:1 methanol:tetrahydrofuran (10 mL) and 4N aqueous lithium hydroxide solution (0.29 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-{[3,5-bis(trifluoromethyl)benzoyl]amino}benzoic acid (0.054 g, 22%) as a white solid. mp=205-206° C. (dec). 1H NMR (500 MHz, DMSO-d6); δ 13.70 (bs, 1H), 12.70 (bs, 1H), 8.51 (s, 1H), 8.43 (s, 1H), 8.32 (d, 2H), 8.00 (d, 1H), 7.67-7.64 (AA′BB′, 4H), 7.45 (t, 2H), 7.37 (t, 1H), 6.84 (d, 1H), 4.31 (t, 2H), 4.22 (t, 2H), 2.18 (m, 2H). Mass spec (MW 630.54); (ES+) m/z 630.96, (ES−) m/z 629.39. Elemental analysis; Calculated for C32H24F6N2O5: C, 60.96; H, 3.84; N, 4.44. Found: C, 60.10; H, 3.57; N, 4.18.

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-dfea9fa11df040c1bd3dcb08317c9abe
Source dataset
uspto-grants-2008_09
Patent number
US07420083B2

Reaction notes

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