2-Nitro-N-[(prop-2-en-1-yl)oxy]benzene-1-sulfonamide → (2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-3,4-dimethyl-5,6-dihydropyridine-1 (2H)-carboxylate

HRID 627207Notes

Reaction equation

HRID 627207 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]1[C:15]([CH3:16])=[C:14]([CH3:17])[C@H:13](O)[CH2:12][N:11]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:26]([O:29][NH:30][S:31]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[N+:40]([O-:42])=[O:41])(=[O:33])=[O:32])[CH:27]=[CH2:28].C(ON([C@H]1CN(C(OC(C)(C)C)=O)[C@H](CO[Si](C(C)(C)C)(C)C)C=C1C)S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O)C=C>>[CH2:26]([O:29][N:30]([C@H:13]1[CH2:12][N:11]([C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[C@H:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3])[C:15]([CH3:16])=[C:14]1[CH3:17])[S:31]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[N+:40]([O-:42])=[O:41])(=[O:33])=[O:32])[CH:27]=[CH2:28]

Participants

4

Reactant 3

HCID 154979112-Nitro-N-[(prop-2-en-1-yl)oxy]benzene-1-sulfonamide2×HCID 89852353(2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-5-hydroxy-3,4-dimethyl-5,6-dihydropyridine-1(2H)-carboxylate2×HCID 89852484(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-4-methyl-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 89852224(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-3,4-dimethyl-5,6-dihydropyridine-1 (2H)-carboxylateYield 110.5%

Procedure

The title compound was prepared from (2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-5-hydroxy-3,4-dimethyl-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 191, 1.73 g, 4.66 mmol) and N-(allyloxy)-2-nitrobenzenesulfonamide (Intermediate 9, 1.26 g, 4.89 mmol) following the procedure described for Intermediate 10. Silica gel chromatography (0%-20% ethyl acetate/hexanes) afforded the desired product as an off-white solid (3.15 g, 100%).

Sources & evidence

ORD record
ord-e056780fa6114717afb4ae5fc5dc9b86
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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