Triphenylphosphine → tert-butyl 3-(4-{{[2',6'-dimethyl-4'-(tetrahydro-2H-thiopyran-4-yloxy)biphenyl-3-yl]methyl}[(2-nitrophenyl)sulfonyl]amino}-2-fluorophenyl)propanoate

HRID 508080

반응식

HRID 508080 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].[S:46]1[CH2:51][CH2:50][CH:49](O)[CH2:48][CH2:47]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:36][C:29]1[CH:30]=[C:31]([O:35][CH:49]2[CH2:50][CH2:51][S:46][CH2:47][CH2:48]2)[CH:32]=[C:33]([CH3:34])[C:28]=1[C:24]1[CH:25]=[CH:26][CH:27]=[C:22]([CH2:21][N:8]([S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N+:18]([O-:20])=[O:19])(=[O:10])=[O:11])[C:6]2[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]=2)[CH:23]=1

참가 물질

6

반응물 4

HCID 11776Triphenylphosphine2회HCID 220568ethyl N-ethoxycarbonyliminocarbamate2회HCID 576296Tetrahydro-2H-thiopyran-4-ol2회HCID 23157516Tert-butyl 3-(2-fluoro-4-{[(4'-hydroxy-2',6'-dimethylbiphenyl-3-yl)methyl][(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate

생성물 1

HCID 23157629tert-butyl 3-(4-{{[2',6'-dimethyl-4'-(tetrahydro-2H-thiopyran-4-yloxy)biphenyl-3-yl]methyl}[(2-nitrophenyl)sulfonyl]amino}-2-fluorophenyl)propanoate수율 100.7%

시약·촉매·용매 1

HCID 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 (3.0 g, 4.73 mmol), tetrahydro-2H-thiopyran-4-ol (0.62 g, 5.20 mmol) and triphenylphosphine (1.36 g, 5.20 mmol) in tetrahydrofuran (60 mL) was added diethyl azodicarboxylate (40% toluene solution, 2.79 mL, 6.15 mmol) under stirring at room temperature, and the mixture was stirred for 16 hr. To the reaction mixture were added reagents (tetrahydro-2H-thiopyran-4-ol, triphenylphosphine and diethyl azodicarboxylate) in a half amount as mentioned above, and the mixture was further stirred for 8 hr. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=2/1) to give the title compound (3.5 g, yield 100%) as a pale-yellow oil.

후처리

  1. stirringthe mixture was stirred for 16 hr
  2. stirringwas further stirred for 8 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. 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-d1ee30167d314135a42ac440efa83f26
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786165B2

연결된 노트

불러오는 중…