2-(Ethylthio)ethanol → Tert-butyl 3-(4-{({4'-[2-(ethylthio)ethoxy]-2',6'-dimethylbiphenyl-3-yl}methyl)[(2-nitrophenyl)sulfonyl]amino}-2-fluorophenyl)propanoate

HRID 508062

반응식

HRID 508062 반응식
[F:1][C:2]1[CH:7]=[C:6]([N:8]([CH2:21][C:22]2[CH:23]=[C:24]([C:28]3[C:33]([CH3:34])=[CH:32][C:31]([OH:35])=[CH:30][C:29]=3[CH3:36])[CH:25]=[CH:26][CH:27]=2)[S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N+:18]([O-:20])=[O:19])(=[O:11])=[O:10])[CH:5]=[CH:4][C:3]=1[CH2:37][CH2:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40].[CH2:46]([S:48][CH2:49][CH2:50]O)[CH3:47].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1.C(OCC)C>[CH2:46]([S:48][CH2:49][CH2:50][O:35][C:31]1[CH:32]=[C:33]([CH3:34])[C:28]([C:24]2[CH:25]=[CH:26][CH:27]=[C:22]([CH2:21][N:8]([S:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N+:18]([O-:20])=[O:19])(=[O:10])=[O:11])[C:6]3[CH:5]=[CH:4][C:3]([CH2:37][CH2:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[C:2]([F:1])[CH:7]=3)[CH:23]=2)=[C:29]([CH3:36])[CH:30]=1)[CH3:47]

참가 물질

7

반응물 4

HCID 80752-(Ethylthio)ethanol2회HCID 13831Tributylphosphine2회HCID 730421,1'-(Azodicarbonyl)dipiperidine2회HCID 23157516Tert-butyl 3-(2-fluoro-4-{[(4'-hydroxy-2',6'-dimethylbiphenyl-3-yl)methyl][(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate

생성물 1

HCID 23157539Tert-butyl 3-(4-{({4'-[2-(ethylthio)ethoxy]-2',6'-dimethylbiphenyl-3-yl}methyl)[(2-nitrophenyl)sulfonyl]amino}-2-fluorophenyl)propanoate수율 86.1%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of tert-butyl 3-(2-fluoro-4-{[(4′-hydroxy-2′,6′-dimethylbiphenyl-3-yl)methyl][(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate (2.0 g, 3.15 mmol), 2-(ethylthio)ethanol (0.37 mL, 3.47 mmol) and tributylphosphine (1.18 mL, 4.73 mmol) in tetrahydrofuran (40 mL) was added 1,1′-(azodicarbonyl)dipiperidine (1.19 g, 4.73 mmol) under stirring at room temperature, and the mixture was stirred for 16 hr. To the reaction mixture were added reagents (2-(ethylthio)ethanol, tributylphosphine and 1,1′-(azodicarbonyl)dipiperidine) in a half amount as above, and the mixture was further stirred for 8 hr. The reaction mixture was diluted with diethyl ether, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=2/1) to give the title compound (1.96 g, yield 86%) as a yellow oil.

후처리

  1. stirringthe mixture was stirred for 16 hr
  2. stirringwas further stirred for 8 hr
  3. filtrationthe insoluble material was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=2/1)

출처 및 근거

ORD 기록
ord-0db48da2ef494ac3936086851a8b355b
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786165B2

연결된 노트

불러오는 중…