(2S,5R)-5-(allyloxyamino)-3-isopropyl-1,2,5,6-tetrahydropyridine-2-carboxamide → (2S,5R)-6-(allyloxy)-3-isopropyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide

HRID 627139Notes

Reaction equation

HRID 627139 reaction equation
[CH2:1]([O:4]N1C(=O)N2C[C@H]1C=C(C)[C@H]2C(N)=O)C=C.[CH2:18]([O:21][NH:22][C@H:23]1[CH2:28][NH:27][C@H:26]([C:29]([NH2:31])=[O:30])[C:25]([CH:32]([CH3:34])[CH3:33])=[CH:24]1)[CH:19]=[CH2:20]>>[CH2:18]([O:21][N:22]1[C:1](=[O:4])[N:27]2[CH2:28][C@H:23]1[CH:24]=[C:25]([CH:32]([CH3:34])[CH3:33])[C@H:26]2[C:29]([NH2:31])=[O:30])[CH:19]=[CH2:20]

Participants

3

Reactant 2

HCID 89852416(2S,5R)-5-(allyloxyamino)-3-isopropyl-1,2,5,6-tetrahydropyridine-2-carboxamide2×HCID 117940228(2S,5R)-6-(allyloxy)-3-methyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide

Product 1

HCID 89852037(2S,5R)-6-(allyloxy)-3-isopropyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamideYield 77%

Procedure

(2S,5R)-6-(allyloxy)-3-isopropyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide (0.46 mg, 77%) was prepared a similar manner as described in Intermediate 86 as a pale yellow oil, using (2S,5R)-5-(allyloxyamino)-3-isopropyl-1,2,5,6-tetrahydropyridine-2-carboxamide (Intermediate 96, 0.54 mg, 0.23 mmol) as a starting material.

Sources & evidence

ORD record
ord-58af91c0f6c34f90837ef9cb9066aec6
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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