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Triphenylphosphine → (2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-3-(2-((tert-butyldimethylsilyl)oxy)ethyl)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 627285
ノート
印刷プレビュー

反応式

HRID 627285 の反応式
OC1CN(C([O-])=O)CC=C1.[Si:11]([O:18][CH2:19][CH2:20][C:21]1[C@@H:22]([CH2:35][O:36][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])[N:23]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][C@@H:25](O)[CH:26]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:63]([O:66][NH:67][S:68]([C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][C:72]=1[N+:77]([O-:79])=[O:78])(=[O:70])=[O:69])[CH:64]=[CH2:65].N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1(C)C=CC=CC=1>[CH2:63]([O:66][N:67]([C@H:25]1[CH2:24][N:23]([C:28]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29])[C@H:22]([CH2:35][O:36][Si:37]([C:40]([CH3:41])([CH3:43])[CH3:42])([CH3:39])[CH3:38])[C:21]([CH2:20][CH2:19][O:18][Si:11]([C:14]([CH3:15])([CH3:16])[CH3:17])([CH3:12])[CH3:13])=[CH:26]1)[S:68]([C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][C:72]=1[N+:77]([O-:79])=[O:78])(=[O:70])=[O:69])[CH:64]=[CH2:65]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 15497911N-(Allyloxy)-2-nitrobenzenesulfonamideHCID 218741495-hydroxy-5,6-dihydropyridine-1(2H)-carboxylateHCID 89852358(2S,5S)-tert-butyl 3-(2-((tert-butyldimethylsilyl)oxy)ethyl)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-hydroxy-5,6-dihydropyridine-1(2H)-carboxylate

生成物 1

HCID 131735303(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-3-(2-((tert-butyldimethylsilyl)oxy)ethyl)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5,6-dihydropyridine-1(2H)-carboxylate収率 69.2%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of (2S,5S)-tert-butyl 3-(2-((tert-butyldimethylsilyl)oxy)ethyl)-2-((tert-butyldimethylsilyl)oxy)methyl)-5-hydroxy-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 281, 7.33 g, 14.61 mmol) in toluene (100 mL) at room temperature was added triphenylphosphine (4.58 g, 17.53 mmol), N-(allyloxy)-2-nitrobenzenesulfonamide (3.77 g, 14.61 mmol) and diisopropyl azodicarboxylate (3.45 mL, 17.53 mmol). The reaction mixture was stirred overnight at room temperature then concentrated. The resulting oil was triturated with hexane and filtered to remove triphenylphosphine oxide. The filtrate was concentrated onto silica gel. Silica gel chromatography (0%-20% ethyl acetate/hexanes) afforded the title compound (7.5 g, 69.2%) as a light yellow oil.

後処理

  1. concentrationthen concentrated
  2. customThe resulting oil was triturated with hexane
  3. filtrationfiltered
  4. customto remove triphenylphosphine oxide
  5. concentrationThe filtrate was concentrated onto silica gel

出典と根拠

ORDレコード
ord-0152ac7abb524fe2a19596dee5b12c2c
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09309245B2

反応ノート

読み込み中…

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