(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-4-(prop-1-en-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate → N-(allyloxy)-N-((3R,6S)-6-((tert-butyldimethylsilyloxy)methyl)-4-(prop-1-en-2-yl)-1,2,3,6-tetrahydropyridin-3-yl)-2-nitrobenzenesulfonamide

HRID 627107Notes

Reaction equation

HRID 627107 reaction equation
[CH2:1]([O:4][N:5]([C@H:18]1[CH2:23][N:22](C(OC(C)(C)C)=O)[C@H:21]([CH2:31][O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[CH:20]=[C:19]1[C:40]([CH3:42])=[CH2:41])[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3].C(ON([C@H]1CN[C@H](C(N)=O)C=C1C)S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O)C=C>>[CH2:1]([O:4][N:5]([C@@H:18]1[C:19]([C:40]([CH3:42])=[CH2:41])=[CH:20][C@@H:21]([CH2:31][O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[NH:22][CH2:23]1)[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 89852307(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-4-(prop-1-en-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate2×HCID 117940244(2S,5R)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-methyl-1,2,5,6-tetrahydropyridine-2-carboxamide

Product 1

HCID 89852508N-(allyloxy)-N-((3R,6S)-6-((tert-butyldimethylsilyloxy)methyl)-4-(prop-1-en-2-yl)-1,2,3,6-tetrahydropyridin-3-yl)-2-nitrobenzenesulfonamide

Procedure

The title compound was prepared from (2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-4-(prop-1-en-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 54, 3.04 g, 4.87 mmol) following the procedure described for Intermediate 21. The desired product was obtained as an orange oil (2.53 g, 99%).

Sources & evidence

ORD record
ord-65d3cc174737428c81e36b7fa121a131
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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