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)-4-carbamoyl-5,6-dihydropyridine-1(2H)-carboxylate

HRID 627144Notes

Reaction equation

HRID 627144 reaction equation
[Si](OC[C@@H]1C=C(C(=O)N)[C@H](O)CN1C(OC(C)(C)C)=O)(C(C)(C)C)(C)C.[CH2:27]([O:30][N:31]([C@H:47]1[CH2:52][N:51]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[C@H:50]([CH2:60][O:61][Si:62]([C:65]([CH3:68])([CH3:67])[CH3:66])([CH3:64])[CH3:63])[CH:49]=[C:48]1[C:69](=[O:71])[NH2:70])[S:32]([C:35]1[CH:40]=[CH:39][C:38]([N+]([O-])=O)=[CH:37][C:36]=1[N+:44]([O-:46])=[O:45])(=[O:34])=[O:33])[CH:28]=[CH2:29].C(ONS(C1C=CC=CC=1[N+]([O-])=O)(=O)=O)C=C.C(ONS(C1C=CC([N+]([O-])=O)=CC=1[N+]([O-])=O)(=O)=O)C=C>>[CH2:27]([O:30][N:31]([C@H:47]1[CH2:52][N:51]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[C@H:50]([CH2:60][O:61][Si:62]([C:65]([CH3:68])([CH3:67])[CH3:66])([CH3:63])[CH3:64])[CH:49]=[C:48]1[C:69](=[O:71])[NH2:70])[S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[N+:44]([O-:46])=[O:45])(=[O:34])=[O:33])[CH:28]=[CH2:29]

Participants

5

Reactant 4

HCID 154979112-Nitro-N-[(prop-2-en-1-yl)oxy]benzene-1-sulfonamide2×HCID 89851401N-(allyloxy)-2,4-dinitrobenzenesulfonamideHCID 89852199(2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-carbamoyl-5-hydroxy-5,6-dihydropyridine-1(2H)-carboxylate3×HCID 89852350(2S,5R)-tert-butyl 5-(N-(allyloxy)-2,4-dinitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-4-carbamoyl-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 89852378(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-4-carbamoyl-5,6-dihydropyridine-1(2H)-carboxylateYield 74%

Procedure

The title compound (4.0 g, 74%) was prepared from (2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-carbamoyl-5-hydroxy-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 104, 3.36 g, 8.69 mmol) using the same procedure to prepare Intermediate 105 from Intermediate 104, but using N-(allyloxy)-2-nitrobenzenesulfonamide (Intermediate 9, 2.24 g, 8.69 mmol) as a reagent in place of N-(allyloxy)-2,4-dinitrobenzenesulfonamide.

Sources & evidence

ORD record
ord-6f03f57a1b434a248a60b9be412fa9be
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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