HCID 86676545, 화합물 → 3,5-diaminobenzyl (2E)-3-(4-{difluoro[4-(4,4,4-trifluorobutoxy)phenyl]-methoxy}phenyl)prop-2-enoate

HRID 511708노트

반응식

HRID 511708 반응식
[F:1][C:2]([F:42])([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][CH2:37][C:38]([F:41])([F:40])[F:39])=[CH:30][CH:29]=1)[O:3][C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]([O:14][CH2:15][C:16]2[CH:21]=[C:20]([N+:22]([O-])=O)[CH:19]=[C:18]([N+:25]([O-])=O)[CH:17]=2)=[O:13])=[CH:6][CH:5]=1>CN(C)C=O.O.[Zn]>[F:1][C:2]([F:42])([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][CH2:37][C:38]([F:41])([F:40])[F:39])=[CH:30][CH:29]=1)[O:3][C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]([O:14][CH2:15][C:16]2[CH:21]=[C:20]([NH2:22])[CH:19]=[C:18]([NH2:25])[CH:17]=2)=[O:13])=[CH:6][CH:5]=1

참가 물질

5

반응물 1

HCID 86676545HCID 86676545, 화합물

생성물 1

HCID 866765463,5-diaminobenzyl (2E)-3-(4-{difluoro[4-(4,4,4-trifluorobutoxy)phenyl]-methoxy}phenyl)prop-2-enoate수율 70.1%

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

4.99 g (8.38 mmol) of 3,5-dinitrobenzyl (2E)-3-(4-{difluoro[4-(4,4,4-trifluorobutoxy)phenyl]-methoxy}phenyl)prop-2-enoate are 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 200 g silica gel using toluene:ethyl acetate 1:3 as eluent and crystallization from ethyl acetate:hexane mixture yields 3.15 g of 3,5-diaminobenzyl (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 200 g silica gel
  9. customcrystallization from ethyl acetate

출처 및 근거

ORD 기록
ord-1633a7bfa85544afaf05fae6e89dd47d
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09097938B2

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