(2R,5R)-5-(allyloxyamino)-4-methyl-1,2,5,6-tetrahydropyridine-2-carboxamide → (2S,5R)-tert-butyl 5-(benzyloxyamino)-2-carbamoyl-4-(2-nitroethyl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 627236Notes

Reaction equation

HRID 627236 reaction equation
[CH2:1]([O:8][N:9]([C@H:22]1[CH2:27][N:26]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C@H:25]([C:35](=[O:37])[NH2:36])[CH:24]=[C:23]1[CH2:38][CH2:39][N+:40]([O-:42])=[O:41])S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(ON[C@H]1CN[C@@H](C(N)=O)C=C1C)C=C>>[CH2:1]([O:8][NH:9][C@H:22]1[CH2:27][N:26]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C@H:25]([C:35](=[O:37])[NH2:36])[CH:24]=[C:23]1[CH2:38][CH2:39][N+:40]([O-:42])=[O:41])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 89851806(2R,5R)-5-(allyloxyamino)-4-methyl-1,2,5,6-tetrahydropyridine-2-carboxamideHCID 89852544(2S,5R)-tert-butyl 5-(N-(benzyloxy)-2-nitrophenylsulfonamido)-2-carbamoyl-4-(2-nitroethyl)-5,6-dihydropyridine-1(2H)-carboxylate2×

Product 1

HCID 89852452(2S,5R)-tert-butyl 5-(benzyloxyamino)-2-carbamoyl-4-(2-nitroethyl)-5,6-dihydropyridine-1(2H)-carboxylate

Procedure

The desired product was prepared from (2S,5R)-tert-butyl 5-(N-(benzyloxy)-2-nitrophenylsulfonamido)-2-carbamoyl-4-(2-nitroethyl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 223, 2 g, 3.30 mmol) following the procedure described for Intermediate 22. The desired product was obtained as yellow oil (0.8 g, 68%).

Sources & evidence

ORD record
ord-92c9f20cf1fe467dbbfb17f417fb35ed
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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