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

HRID 29678
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HRID 29678 반응식
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
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f50fb79c548e4caba5fa44954f53e739
출처 데이터셋
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07420083B2

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