Hexamethylphosphoramide → p-(t-Butyl)benzyl 3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

HRID 1105863Notes

Reaction equation

HRID 1105863 reaction equation
[Cl:1][C:2]1[CH2:8][CH:7]2[N:4]([C:5](=[O:9])[CH2:6]2)[C:3]=1[C:10]([O-:12])=[O:11].[Na+].[C:14]([C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15].CN(C)P(N(C)C)(N(C)C)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH2:8][CH:7]2[N:4]([C:5](=[O:9])[CH2:6]2)[C:3]=1[C:10]([O:12][CH2:22][C:21]1[CH:24]=[CH:25][C:18]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:19][CH:20]=1)=[O:11]

Participants

5

Reactant 3

HCID 12679HexamethylphosphoramideHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzeneHCID 23672728Sodium 3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Product 1

HCID 20555241p-(t-Butyl)benzyl 3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of sodium 3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate (20 mg), p-(t-butyl)benzyl bromide (34 mg), and anhydrous hexamethylphosphoramide (0.4 ml) is stirred under a nitrogen atmosphere at room temperature for 2.5 hrs. The mixture is diluted with toluene (5 ml), washed with water (5×2 ml) and brine, dried with MgSO4, filtered, and concentrated in vacuo. Chromatography of the residue on a silica gel plate yields p-(t-butyl)benzyl 3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

Workup

  1. washwashed with water (5×2 ml) and brine
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-03ab253db4914317bfd20e3850639605
Source dataset
uspto-grants-1982_01
Patent number
US04310538

Reaction notes

Loading…