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

HRID 29682노트

반응식

HRID 29682 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 113994382-[[3,5-bis(trifluoromethyl)benzoyl]amino]-4-[3-[(E)-(4-phenylphenyl)methylideneamino]oxypropoxy]benzoic acid수율 22%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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-{[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.

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-dfea9fa11df040c1bd3dcb08317c9abe
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07420083B2

반응 노트

불러오는 중…