Bromomethyl pivalate → Pivaloyloxymethyl 1-azabicyclo[3.2.0]heptan-3,7-dione-2-carboxylate

HRID 2198446Notes

Reaction equation

HRID 2198446 reaction equation
[N:1]12[C:7](=[O:8])[CH2:6][CH:5]1[CH2:4][C:3](=[O:9])[CH:2]2[C:10]([O-:12])=[O:11].[Na+].[C:14]([O:20][CH2:21]Br)(=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16]>CN(C)P(N(C)C)(N(C)C)=O.C1C=CC=CC=1>[N:1]12[C:7](=[O:8])[CH2:6][CH:5]1[CH2:4][C:3](=[O:9])[CH:2]2[C:10]([O:12][CH2:21][O:20][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])=[O:11]

Participants

5

Reactant 2

HCID 15916453Bromomethyl pivalateHCID 23692747Sodium 1-azabicyclo[3.2.0]heptan-3,7-dione-2-carboxylate

Product 1

HCID 20520258Pivaloyloxymethyl 1-azabicyclo[3.2.0]heptan-3,7-dione-2-carboxylate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

To a stirring suspension of sodium 1-azabicyclo[3.2.0]heptan-3,7-dione-2-carboxylate (20 mg) in anhydrous hexamethylphosphoramide (0.5 ml) is added bromomethyl pivalate (35 mg). The resulting mixture is stirred at room temperature for 2 hrs, then diluted with benzene (5 ml) and washed thoroughly with H2O (5×2 ml) and brine. The benzene solution is dried with MgSO4, filtered, and concentrated under reduced pressure. Preparative tlc of the residue on a silica gel GF plate provides pivaloyloxymethyl 1-azabicyclo[3.2.0]heptan-3,7-dione-2-carboxylate.

Workup

  1. washwashed thoroughly with H2O (5×2 ml) and brine
  2. dry with materialThe benzene solution is dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2a2a16359a814ceca8fe66d435c18e20
Source dataset
uspto-grants-1982_11
Patent number
US04357342

Reaction notes

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