4-(2-Chloroethyl)morpholine → HCID 69200734, compound

HRID 2376673Notes

Reaction equation

HRID 2376673 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:15][C@H:14]3[N:11]([C:12](=[O:19])[C@@H:13]3[C@H:16]([OH:18])[CH3:17])[C:10]=2[C:20]([O-:22])=[O:21])=[CH:5][CH:4]=1)#[N:2].[Na+].Cl[CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:15][C@H:14]3[N:11]([C:12](=[O:19])[C@@H:13]3[C@H:16]([OH:18])[CH3:17])[C:10]=2[C:20]([O:22][CH2:25][CH2:26][N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[O:21])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 767274-(2-Chloroethyl)morpholineHCID 58691150HCID 58691150, compound

Product 1

HCID 69200734HCID 69200734, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

Sodium (5R,6S)-3-(4-cyanophenyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.2 g) in dry DMF (4.0 ml) was ice-cooled. Thereto ware added tetrabutylammonium iodide (0.53 g), and 4-(2-chloroethyl)-morpholine (1M toluene, 8 mL), and the mixture was stirred. Thirty minutes later, after removal of the bath the mixture was stirred for 48 hours and thereto was added ethyl acetate. The mixture was washed succesively with aqueous phosphate buffer (pH 6.86), water and brine. The organic layer was dried over sodium sulfate, concentrated, and the residue was purified with silica gel column chromatography (chloroform:methanol=1:0→10:1) to give 2-morpholin-4-ylethyl(5R,6S)-3-(4-cyanophenyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.10 g, yield 33%).

Workup

  1. temperaturecooled
  2. customThirty minutes later, after removal of the bath the mixture
  3. stirringwas stirred for 48 hours
  4. additionwas added ethyl acetate
  5. washThe mixture was washed succesively with aqueous phosphate buffer (pH 6.86), water and brine
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated
  8. customthe residue was purified with silica gel column chromatography (chloroform:methanol=1:0→10:1)

Sources & evidence

ORD record
ord-d80fb79e57ef4fb79bb203410bbd490b
Source dataset
uspto-grants-2008_12
Patent number
US07468364B2

Reaction notes

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