(2S,5R)-6-(allyloxy)-2-((tert-butyldimethylsilyloxy)methyl)-4-methyl-1,6-diazabicyclo[3.2.1]oct-3-en-7-one → (2S,5R)-6-(allyloxy)-2-(methoxymethyl)-N-methyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-4-carboxamide

HRID 627267Notes

Reaction equation

HRID 627267 reaction equation
[CH2:1]([O:4]N1C(=O)N2C[C@H]1C(C)=C[C@H]2CO[Si](C(C)(C)C)(C)C)C=C.[CH2:24]([O:27][NH:28][C@@H:29]1[C:34]([C:35]([NH:37][CH3:38])=[O:36])=[CH:33][C@@H:32]([CH2:39][O:40][CH3:41])[NH:31][CH2:30]1)[CH:25]=[CH2:26]>>[CH2:24]([O:27][N:28]1[C:1](=[O:4])[N:31]2[CH2:30][C@H:29]1[C:34]([C:35]([NH:37][CH3:38])=[O:36])=[CH:33][C@H:32]2[CH2:39][O:40][CH3:41])[CH:25]=[CH2:26]

Participants

3

Reactant 2

HCID 89852160(2S,5R)-6-(allyloxy)-2-((tert-butyldimethylsilyloxy)methyl)-4-methyl-1,6-diazabicyclo[3.2.1]oct-3-en-7-oneHCID 89852327(3R,6S)-3-(allyloxyamino)-6-(methoxymethyl)-N-methyl-1,2,3,6-tetrahydropyridine-4-carboxamide2×

Product 1

HCID 89852410(2S,5R)-6-(allyloxy)-2-(methoxymethyl)-N-methyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-4-carboxamideYield 68%

Procedure

The title compound (0.28 g, 68%) was prepared according to the procedure described for Intermediate 13, starting from (3R,6S)-3-(allyloxyamino)-6-(methoxymethyl)-N-methyl-1,2,3,6-tetrahydropyridine-4-carboxamide (Intermediate 258, 0.52 g)

Sources & evidence

ORD record
ord-117a60bb1a1940a2a23bf8f07a767591
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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