Triphenylphosphine → (2S,5R)-tert-butyl 5-(N-(allyloxy)-2,4-dinitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 627156노트

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HRID 627156 반응식
[Si:1]([O:8][CH2:9][C@@H:10]1[CH:15]=[CH:14][C@H:13](O)[CH2:12][N:11]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH2:43]([O:46][NH:47][S:48]([C:51]1[CH:56]=[CH:55][C:54]([N+:57]([O-:59])=[O:58])=[CH:53][C:52]=1[N+:60]([O-:62])=[O:61])(=[O:50])=[O:49])[CH:44]=[CH2:45].N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1(C)C=CC=CC=1>[CH2:43]([O:46][N:47]([C@H:13]1[CH2:12][N:11]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[C@H:10]([CH2:9][O:8][Si:1]([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:3])[CH3:2])[CH:15]=[CH:14]1)[S:48]([C:51]1[CH:56]=[CH:55][C:54]([N+:57]([O-:59])=[O:58])=[CH:53][C:52]=1[N+:60]([O-:62])=[O:61])(=[O:50])=[O:49])[CH:44]=[CH2:45]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 89851401N-(allyloxy)-2,4-dinitrobenzenesulfonamideHCID 89852438(2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-5-hydroxy-5,6-dihydropyridine-1(2H)-carboxylate2회

생성물 1

HCID 89852173(2S,5R)-tert-butyl 5-(N-(allyloxy)-2,4-dinitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-5,6-dihydropyridine-1(2H)-carboxylate수율 96.2%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a stirred solution of (2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-5-hydroxy-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 125, 17.50 g, 50.94 mmol), phosphorus triphenyl (14.70 g, 56.04 mmol), N-(allyloxy)-2,4-dinitrobenzenesulfonamide (16.22 g, 53.49 mmol) in toluene (380 mL) was added diisopropyl azodicarboxylate (11.03 ml, 56.04 mmol) at room temperature. The reaction mixture was stirred at rt overnight. The mixture was concentrated and the residue was purified by silica gel column (220 g, 0-40% Hex/EA) to give the desired product (30.8 g) as a yellow gum.

후처리

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by silica gel column (220 g, 0-40% Hex/EA)

출처 및 근거

ORD 기록
ord-696645bc335f444caf17401c26cc0f68
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309245B2

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