N-(Benzyloxy)-2-nitrobenzenesulfonamide → (2S,5R)-tert-butyl 5-(N-(benzyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-4-(2-nitroethyl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 627232Notes

Reaction equation

HRID 627232 reaction equation
C(ON([C@H]1CN(C(OC(C)(C)C)=O)[C@H](CO[Si](C(C)(C)C)(C)C)C(C)=C1)S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O)C=C.[Si:41]([O:48][CH2:49][C@@H:50]1[CH:55]=[C:54]([CH2:56][CH2:57][N+:58]([O-:60])=[O:59])[C@H:53](O)[CH2:52][N:51]1[C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:43])[CH3:42].[CH2:69]([O:76][NH:77][S:78]([C:81]1[CH:86]=[CH:85][CH:84]=[CH:83][C:82]=1[N+:87]([O-:89])=[O:88])(=[O:80])=[O:79])[C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1>>[CH2:69]([O:76][N:77]([C@H:53]1[CH2:52][N:51]([C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])[C@H:50]([CH2:49][O:48][Si:41]([C:44]([CH3:47])([CH3:45])[CH3:46])([CH3:43])[CH3:42])[CH:55]=[C:54]1[CH2:56][CH2:57][N+:58]([O-:60])=[O:59])[S:78]([C:81]1[CH:86]=[CH:85][CH:84]=[CH:83][C:82]=1[N+:87]([O-:89])=[O:88])(=[O:80])=[O:79])[C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1

Participants

4

Reactant 3

HCID 9839578N-(Benzyloxy)-2-nitrobenzenesulfonamideHCID 89852556(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-3-methyl-5,6-dihydropyridine-1(2H)-carboxylateHCID 89852570(2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-5-hydroxy-4-(2-nitroethyl)-5,6-dihydropyridine-1 (2H)-carboxylate2×

Product 1

HCID 89852745(2S,5R)-tert-butyl 5-(N-(benzyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-4-(2-nitroethyl)-5,6-dihydropyridine-1(2H)-carboxylate

Procedure

The title compound was prepared as a pale yellow oil (5 g, 30%) according to the procedure described for Intermediate 80, from (2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-5-hydroxy-4-(2-nitroethyl)-5,6-dihydropyridine-1 (2H)-carboxylate (Intermediate 219, 6.73 g, 16.3 mmol) and N-(benzyloxy)-2-nitrobenzenesulfonamide (7.40 g, 24.00 mmol).

Sources & evidence

ORD record
ord-8f2326d1e85047d0a6742fd0ce41a2e0
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

Loading…