Bromomethyl pivalate → Pivaloyloxymethyl 3-acetoxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

HRID 1164336Notes

Reaction equation

HRID 1164336 reaction equation
[C:1]([O:4][C:5]1[CH2:11][CH:10]2[N:7]([C:8](=[O:12])[CH2:9]2)[C:6]=1[C:13]([O-:15])=[O:14])(=[O:3])[CH3:2].[Na+].[C:17]([O:23][CH2:24]Br)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19]>CN(C)P(N(C)C)(N(C)C)=O.C1(C)C=CC=CC=1>[C:1]([O:4][C:5]1[CH2:11][CH:10]2[N:7]([C:8](=[O:12])[CH2:9]2)[C:6]=1[C:13]([O:15][CH2:24][O:23][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])=[O:14])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 15916453Bromomethyl pivalateHCID 23682168Sodium 3-acetoxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Product 1

HCID 20511949Pivaloyloxymethyl 3-acetoxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

A mixture of sodium 3-acetoxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate (23 mg) and bromomethyl pivalate (29 mg) in hexamethylphosphoramide (0.5 ml) is stirred at room temperature and under a N2 atmosphere for 2.5 hrs. The mixture is diluted with toluene (10 ml), washed with H2O (5×2 ml) and brine, dried with MgSO4, filtered, and evaporated in vacuo. The residue is purified by silica gel plc to afford pivaloyloxymethyl 3-acetoxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

Workup

  1. washwashed with H2O (5×2 ml) and brine
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue is purified by silica gel plc

Sources & evidence

ORD record
ord-0cefbe7978ae464c84d1b6b1ee4e4765
Source dataset
uspto-grants-1983_01
Patent number
US04369187

Reaction notes

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