Sodium hydride → Methyl (4-methylthio-2-oxoazetidin-1-yl)acetate

HRID 1706131Notes

Reaction equation

HRID 1706131 reaction equation
[CH3:1][S:2][CH:3]1[NH:6][C:5](=[O:7])[CH2:4]1.[H-].[Na+].Br[CH2:11][C:12]([O:14][CH3:15])=[O:13]>CN(C)C=O.O>[CH3:1][S:2][CH:3]1[N:6]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[C:5](=[O:7])[CH2:4]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 126772484-(Methylsulfanyl)azetidin-2-one

Product 1

HCID 13556624Methyl (4-methylthio-2-oxoazetidin-1-yl)acetateYield 63.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

4-Methylthioazetidin-2-one (2.34 g, 20 mmole) was dissolved in dry dimethylformamide (40 ml) and treated at 0°-5° C. with sodium hydride (20 mmole). After 3 minutes methyl bromoacetate (3.37 g, 22 mmole) dissolved in dry dimethylformamide (20 ml) was added and the reaction mixture stirred for 3/4 hour at 0°-5° C. After diluting with water (300 ml), the mixture was extracted with ethyl acetate (3×100 ml) and the extracts combined, washed with water, dried (MgSO4) and evaporated. Chromatography of the residue on silica gel eluting with 30% ethyl acetate in petrolether provided methyl (4-methylthio-2-oxoazetidin-1-yl)acetate (2.4 g, 62%) as a mobile liquid. νmax (CHCl3): 1760 (b), 1410, 1240, 1185 cm-1 ; δ(CDCl3): 2.13 (s, 3H, SCH3); 2.95-3.75 (2H, AB of ABX, CH2); 3.88 (s, 3H, OCH3); 3.93 and 4.23 (2H, main peaks of ABq, J=18 Hz, NCH2) and 5.02 (1H, X of ABX, CH).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate (3×100 ml)
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-14882a4589de4f9584ed39960893e97a
Source dataset
uspto-grants-1980_06
Patent number
US04206120

Reaction notes

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