Water → 4-Nitrobenzyl 2-(4-allylthioazetidin-2-on-1-yl)acetate

HRID 1788833Notes

Reaction equation

HRID 1788833 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([CH2:8]C(Br)C([O-])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:16]([S:19][CH:20]1[NH:23][C:22](=[O:24])[CH2:21]1)[CH:17]=[CH2:18].[C:25](=[O:28])([O-])[O-:26].[K+].[K+].O.[CH3:32]N(C)C=O>>[CH2:16]([S:19][CH:20]1[N:23]([CH2:32][C:25]([O:26][CH2:8][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:15][CH:14]=2)=[O:28])[C:22](=[O:24])[CH2:21]1)[CH:17]=[CH2:18]

Participants

6

Reactant 5

HCID 962WaterHCID 6228Dimethylformamide2×HCID 11430Potassium CarbonateHCID 128496304-Allylthioazetidin-2-oneHCID 225683704-Nitrobenzylbromoacetate

Product 1

HCID 128496314-Nitrobenzyl 2-(4-allylthioazetidin-2-on-1-yl)acetate

Procedure

11.5 g of 4-nitrobenzylbromoacetate in 30 ml of dimethylformamide was added to 5.0 g of 4-allylthioazetidin-2-one dissolved in 70 ml of dimethylformamide with stirring under argon at room temperature. After 5 mins, 10.61 g of potassium carbonate was added to the solution. During the following 20 mins there was a colour change in the mixture from yellow to dark brown. Stirring was continued for a further 3 hours 40 mins. The mixture was then poured into water (300 ml), extracted into ethyl acetate (4×100 ml) and the combined organic extracts washed with water (3×200 ml). The organic layer was dried with MgSO4 and evaporated to leave a yellow oil.

Workup

  1. customDuring the following 20 mins there
  2. stirringStirring
  3. waitwas continued for a further 3 hours 40 mins
  4. extractionextracted into ethyl acetate (4×100 ml)
  5. washthe combined organic extracts washed with water (3×200 ml)
  6. dry with materialThe organic layer was dried with MgSO4
  7. customevaporated
  8. customto leave a yellow oil

Sources & evidence

ORD record
ord-2367364d91d348c0b828b1a5a79f548f
Source dataset
uspto-grants-1987_08
Patent number
US04684640

Reaction notes

Loading…