2-(2,4-dinitrophenyl)-3-{[(2E)-3-(4-{difluoro[4-(4,4,4-trifluorobutoxy)phenyl]methoxy}phenyl)prop-2-enoyl]oxy}propyl (2E)-3-(4-{difluoro[4-(4,4,4-trifluorobutoxy)phenyl]methoxy}phenyl)prop-2-enoate → HCID 86676550, 화합물

HRID 511712노트

반응식

HRID 511712 반응식
[F:1][C:2]([F:73])([C:59]1[CH:64]=[CH:63][C:62]([O:65][CH2:66][CH2:67][CH2:68][C:69]([F:72])([F:71])[F:70])=[CH:61][CH:60]=1)[O:3][C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]([O:14][CH2:15][CH:16]([C:47]2[CH:52]=[CH:51][C:50]([N+:53]([O-])=O)=[CH:49][C:48]=2[N+:56]([O-])=O)[CH2:17][O:18][C:19](=[O:46])/[CH:20]=[CH:21]/[C:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]([F:45])([F:44])[C:30]3[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][CH2:39][C:40]([F:43])([F:42])[F:41])=[CH:32][CH:31]=3)=[CH:24][CH:23]=2)=[O:13])=[CH:6][CH:5]=1>CN(C)C=O.O.[Zn]>[F:1][C:2]([F:73])([C:59]1[CH:64]=[CH:63][C:62]([O:65][CH2:66][CH2:67][CH2:68][C:69]([F:72])([F:71])[F:70])=[CH:61][CH:60]=1)[O:3][C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]([O:14][CH2:15][CH:16]([C:47]2[CH:52]=[CH:51][C:50]([NH2:53])=[CH:49][C:48]=2[NH2:56])[CH2:17][O:18][C:19](=[O:46])/[CH:20]=[CH:21]/[C:22]2[CH:23]=[CH:24][C:25]([O:28][C:29]([F:44])([F:45])[C:30]3[CH:31]=[CH:32][C:33]([O:36][CH2:37][CH2:38][CH2:39][C:40]([F:41])([F:42])[F:43])=[CH:34][CH:35]=3)=[CH:26][CH:27]=2)=[O:13])=[CH:6][CH:5]=1

참가 물질

5

반응물 1

HCID 866765512-(2,4-dinitrophenyl)-3-{[(2E)-3-(4-{difluoro[4-(4,4,4-trifluorobutoxy)phenyl]methoxy}phenyl)prop-2-enoyl]oxy}propyl (2E)-3-(4-{difluoro[4-(4,4,4-trifluorobutoxy)phenyl]methoxy}phenyl)prop-2-enoate

생성물 1

HCID 86676550HCID 86676550, 화합물수율 89.2%

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

8.70 g (8.38 mmol) of 2-(2,4-dinitrophenyl)-3-{[(2E)-3-(4-{difluoro[4-(4,4,4-trifluorobutoxy)phenyl]methoxy}phenyl)prop-2-enoyl]oxy}propyl (2E)-3-(4-{difluoro[4-(4,4,4-trifluorobutoxy)phenyl]methoxy}phenyl)prop-2-enoate is dissolved in a mixture of 54 mL of N,N-dimethylformamide and 6 mL water. 13.9 g (51.4 mmol) ferric chloride hexahydrate are added. 5.60 g (85.7 mmol) zinc powder is added portion wise within 60 minutes. The mixture is allowed to react for 2 hours. The reaction mixture is partitioned between ethyl acetate and water and filtrated. The organic phase is washed repeatedly with water, dried over sodium sulfate, filtrated and concentrated under reduced pressure. Filtration of the residue on 400 g silica gel using toluene:ethyl acetate 1:3 as eluent and crystallization from ethyl acetate:hexane mixture yields 7.32 g of 2-(2,4-diaminophenyl)-3-{[(2E)-3-(4-{difluoro[4-(4,4,4-trifluorobutoxy)phenyl]methoxy}phenyl)prop-2-enoyl]oxy}propyl (2E)-3-(4-{difluoro[4-(4,4,4-trifluorobutoxy)phenyl]methoxy}phenyl)prop-2-enoate as yellow crystals.

후처리

  1. customto react for 2 hours
  2. customThe reaction mixture is partitioned between ethyl acetate and water
  3. filtrationfiltrated
  4. washThe organic phase is washed repeatedly with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltrated
  7. concentrationconcentrated under reduced pressure
  8. filtrationFiltration of the residue on 400 g silica gel
  9. customcrystallization from ethyl acetate

출처 및 근거

ORD 기록
ord-8255c787fe6c4029b9842892dfda095e
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09097938B2

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