Diisopropylethylamine → (2S,5R)-6-(allyloxy)-4-isopropyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide

HRID 627100Notes

Reaction equation

[CH2:1]([O:4][NH:5][C@H:6]1[CH2:11][NH:10][C@H:9]([C:12]([NH2:14])=[O:13])[CH:8]=[C:7]1[CH:15]([CH3:17])[CH3:16])[CH:2]=[CH2:3].C(N(CC)C(C)C)(C)C.[CH2:27]([O:30]N1C(=O)N2C[C@H]1C(C)=C[C@H]2C(N)=O)C=C>>[CH2:1]([O:4][N:5]1[C:27](=[O:30])[N:10]2[CH2:11][C@H:6]1[C:7]([CH:15]([CH3:17])[CH3:16])=[CH:8][C@H:9]2[C:12]([NH2:14])=[O:13])[CH:2]=[CH2:3]

Participants

Reactant 3

HCID 81531Diisopropylethylamine

HCID 89851371HCID 89851371, compound

HCID 89852129(2S,5R)-5-(allyloxyamino)-4-isopropyl-1,2,5,6-tetrahydropyridine-2-carboxamide2×

Product 1

HCID 89852742(2S,5R)-6-(allyloxy)-4-isopropyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide

Procedure

The title compound was prepared from (2S,5R)-5-(allyloxyamino)-4-isopropyl-1,2,5,6-tetrahydropyridine-2-carboxamide (0.0981 g, 0.41 mmol) and N,N-diisopropylethylamine (Intermediate 42, 0.286 mL, 1.64 mmol) following the procedure described for Intermediate 16. The desired product was obtained as a light yellow oil (69 mg, 63%).

Sources & evidence

ORD record: ord-242d92d55279420288179b247c76e4cd
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309245B2

Reaction notes

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