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

HRID 627237Notes

Reaction equation

HRID 627237 reaction equation
[CH2:1]([O:8][NH:9][C@H:10]1[CH2:15][N:14](C(OC(C)(C)C)=O)[C@H:13]([C:23](=[O:25])[NH2:24])[CH:12]=[C:11]1[CH2:26][CH2:27][N+:28]([O-:30])=[O:29])[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)S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O)C=C>>[CH2:1]([O:8][NH:9][C@H:10]1[CH2:15][NH:14][C@H:13]([C:23]([NH2:24])=[O:25])[CH:12]=[C:11]1[CH2:26][CH2:27][N+:28]([O-:30])=[O:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 89852452(2S,5R)-tert-butyl 5-(benzyloxyamino)-2-carbamoyl-4-(2-nitroethyl)-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 89851794(2S,5R)-5-(benzyloxyamino)-4-(2-nitroethyl)-1,2,5,6-tetrahydropyridine-2-carboxamide

Procedure

The title compound was prepared from (2S,5R)-tert-butyl 5-(benzyloxyamino)-2-carbamoyl-4-(2-nitroethyl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 224, 0.800 g, 3.30 mmol) according to the procedure described for Intermediate 21. The desired product was obtained as a yellow oil (0.6 g, 98%).

Sources & evidence

ORD record
ord-a57c2982cf074a889eea9057d23bf444
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

Loading…