Dimethylformamide dimethyl acetal → HCID 178484349, compound

HRID 1406867Notes

Reaction equation

HRID 1406867 reaction equation
CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[CH2:9]([O:16][N:17]1[C:23](=[O:24])[N:22]2[CH2:25][C@H:18]1[CH2:19][CH2:20][C@H:21]2[C:26]([NH2:28])=[O:27])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>O1CCOCC1>[CH2:9]([O:16][N:17]1[C:23](=[O:24])[N:22]2[CH2:25][C@H:18]1[CH2:19][CH2:20][C@H:21]2[C:26](/[N:28]=[CH:3]\[N:4]([CH3:6])[CH3:5])=[O:27])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 57389435(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

Product 1

HCID 178484349HCID 178484349, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Dimethoxy-N,N-dimethylmethanamine (0.97 mL, 7 mmol) was added to a solution of (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carboxamide (1.38 g, 5 mmol) in 1,4-dioxane (20 mL) at rt. The mixture was stiffed at 45-50° C. for 2 hrs under vacuum to remove the methanol formed during the reaction. Then, the reaction mixture was concentrated under vacuum, and the residue was washed with Et2O (2×) and dried to give (2S,5R,Z)-6-(benzyloxy)-N-((dimethylamino)methylene)-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carboxamide (1.33 g, 80%) as a white solid. (ESI-MS (EI+, 331, m/z): [M+H]+.

Workup

  1. customto remove the methanol
  2. customformed during the reaction
  3. concentrationThen, the reaction mixture was concentrated under vacuum
  4. washthe residue was washed with Et2O (2×)
  5. customdried

Sources & evidence

ORD record
ord-3c11687483814165b49aee28e0ee336d
Source dataset
uspto-grants-2014_12
Patent number
US08916709B2

Reaction notes

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