(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-carbamoyl-4-cyclopropyl-5,6-dihydropyridine-1(2H)-carboxylate → (2S,5R)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-cyclopropyl-1,2,5,6-tetrahydropyridine-2-carboxamide

HRID 627276Notes

Reaction equation

HRID 627276 reaction equation
[CH2:1]([O:4][N:5]([C@H:18]1[CH2:23][N:22](C(OC(C)(C)C)=O)[C@H:21]([C:31](=[O:33])[NH2:32])[CH:20]=[C:19]1[CH:34]1[CH2:36][CH2:35]1)[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3].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:4][N:5]([C@H:18]1[CH2:23][NH:22][C@H:21]([C:31]([NH2:32])=[O:33])[CH:20]=[C:19]1[CH:34]1[CH2:35][CH2:36]1)[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 89851980(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-carbamoyl-4-cyclopropyl-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 89852121(2S,5R)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-cyclopropyl-1,2,5,6-tetrahydropyridine-2-carboxamide

Procedure

The title compound was prepared from (2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-carbamoyl-4-cyclopropyl-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 268, 1.47 g, 2.81 mmol) following the procedure described for Intermediate 21. The desired product was obtained as a light yellow foam (0.95 g, 80%).

Sources & evidence

ORD record
ord-0f499bc2273e4b9abb6df6868d72b8c1
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

Loading…