(2S,5R)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-3-isopropyl-1,2,5,6-tetrahydropyridine-2-carboxamide → (2S,5R)-5-(allyloxyamino)-3-isopropyl-1,2,5,6-tetrahydropyridine-2-carboxamide

HRID 627138Notes

Reaction equation

HRID 627138 reaction equation
C(ON[C@H]1CN[C@H](C(N)=O)C(C)=C1)C=C.[CH2:16]([O:19][N:20]([C@H:33]1[CH2:38][NH:37][C@H:36]([C:39]([NH2:41])=[O:40])[C:35]([CH:42]([CH3:44])[CH3:43])=[CH:34]1)S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O)[CH:17]=[CH2:18]>>[CH2:16]([O:19][NH:20][C@H:33]1[CH2:38][NH:37][C@H:36]([C:39]([NH2:41])=[O:40])[C:35]([CH:42]([CH3:44])[CH3:43])=[CH:34]1)[CH:17]=[CH2:18]

Participants

3

Reactant 2

HCID 89852180(2S,5R)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-3-isopropyl-1,2,5,6-tetrahydropyridine-2-carboxamide2×HCID 89852283(2S,5R)-5-(allyloxyamino)-3-methyl-1,2,5,6-tetrahydropyridine-2-carboxamide

Product 1

HCID 89852416(2S,5R)-5-(allyloxyamino)-3-isopropyl-1,2,5,6-tetrahydropyridine-2-carboxamideYield 61%

Procedure

(2S,5R)-5-(allyloxyamino)-3-isopropyl-1,2,5,6-tetrahydropyridine-2-carboxamide (55.0 mg, 61.0%) was prepared a similar manner as described in Intermediate 85 as an off-white solid, using (2S,5R)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-3-isopropyl-1,2,5,6-tetrahydropyridine-2-carboxamide (Intermediate 95, 160 mg, 0.38 mmol) as a starting material.

Sources & evidence

ORD record
ord-9d6e46eab21141939aefff58ebfa4636
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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