Dichloromethane → (4-Allylthio-3-ethylazetidin-2-on-1-yl)acetic acid

HRID 622810Notes

Reaction equation

HRID 622810 reaction equation
[CH2:1]([S:4][CH:5]1[N:8]([CH2:9][C:10]([O:12]C)=[O:11])[C:7](=[O:14])[CH:6]1[CH2:15][CH3:16])[CH:2]=[CH2:3].[OH-].[K+].ClCCl>C(O)C.O>[CH2:1]([S:4][CH:5]1[N:8]([CH2:9][C:10]([OH:12])=[O:11])[C:7](=[O:14])[CH:6]1[CH2:15][CH3:16])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 14797Potassium HydroxideHCID 13106494Methyl (4-allylthio-3-ethylazetidin-2-on-1-yl)acetate

Product 1

HCID 13106496(4-Allylthio-3-ethylazetidin-2-on-1-yl)acetic acidYield 90.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

To a stirred solution of 3 g of methyl 2-(4-allylthio-3-ethylazetidin-2-on-1-yl)acetate in 10 ml of absolute ethanol was added dropwise a solution of 0.9 g of potassium hydroxide in a mixture of 12 ml of ethanol and 1 ml of water. After 5 minutes, the mixture was poured into a mixture of 10 ml of dichloromethane and 20 ml of water. After acidification with 13 ml of 2M HCl, the mixture was extracted with further dichloromethane; the dichloromethane extracts were extracted with saturated sodium bicarbonate solution. These aqueous extracts were acidified to pH 1.5 with 5M HCl and then extracted with dichloromethane. These organic extracts were evaporated to dryness to afford the title compound as a white crystalline solid (2.56 g).

Workup

  1. extractionAfter acidification with 13 ml of 2M HCl, the mixture was extracted with further dichloromethane
  2. extractionthe dichloromethane extracts were extracted with saturated sodium bicarbonate solution
  3. extractionextracted with dichloromethane
  4. customThese organic extracts were evaporated to dryness

Sources & evidence

ORD record
ord-8fcb660784cc4e6b9a9b9209d3b81a96
Source dataset
uspto-grants-1988_09
Patent number
US04772692

Reaction notes

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