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

HRID 627156ノート

反応式

HRID 627156 の反応式
[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]

参加物

6

反応物 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)-carboxylate2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-696645bc335f444caf17401c26cc0f68
出典データセット
uspto-grants-2016_04
特許番号
US09309245B2

反応ノート

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