HCID 89851371, compound → (2S,5R)-6-(allyloxy)-4-(2-amino-2-oxoethyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide

HRID 627200Notes

Reaction equation

HRID 627200 reaction equation
[CH2:1]([O:4][NH:5][CH:6]1[CH2:11][NH:10][C@@H:9]([C:12]([NH2:14])=[O:13])[CH:8]=[C:7]1[CH2:15][C:16]([NH2:18])=[O:17])[CH:2]=[CH2:3].[CH2:19]([O:22]N1C(=O)N2C[C@H]1C(C)=C[C@H]2C(N)=O)C=C>>[CH2:1]([O:4][N:5]1[C:19](=[O:22])[N:10]2[CH2:11][C@H:6]1[C:7]([CH2:15][C:16]([NH2:18])=[O:17])=[CH:8][C@H:9]2[C:12]([NH2:14])=[O:13])[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 89851371HCID 89851371, compoundHCID 89852066(R)-5-(allyloxyamino)-4-(2-amino-2-oxoethyl)-1,2,5,6-tetrahydropyridine-2-carboxamide2×

Product 1

HCID 89852223(2S,5R)-6-(allyloxy)-4-(2-amino-2-oxoethyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide

Conditions

Temperature
0 °C

Procedure

The title compound was prepared from (R)-5-(allyloxyamino)-4-(2-amino-2-oxoethyl)-1,2,5,6-tetrahydropyridine-2-carboxamide (Intermediate 177, 132 mg, 0.52 mmol) following the procedure described for Intermediate 16. The reaction mixture was stirred at 0° C. for 2 h. The volatile was removed under vacuum and the crude was subjected to silica column eluting with 0-100% ethyl acetate/hexanes and then 95% ethyl acetate/5% MeOH to give a pale yellow solid. 62 mg, 43%.

Workup

  1. customThe volatile was removed under vacuum
  2. washeluting with 0-100% ethyl acetate/hexanes
  3. custom95% ethyl acetate/5% MeOH to give a pale yellow solid

Sources & evidence

ORD record
ord-52a0e93d23d34d3c9effba0fb65d2b0e
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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