Sodium Chloride → HCID 54367787, compound

HRID 1719295Notes

Reaction equation

HRID 1719295 reaction equation
C[O:2][C:3]([CH2:9][C@@H:10]1[CH2:13][C:12](=[O:14])[NH:11]1)=[CH:4][C:5]([O:7][CH3:8])=[O:6].[Cl-].[Na+]>Cl>[O:2]=[C:3]([CH2:9][C@@H:10]1[CH2:13][C:12](=[O:14])[NH:11]1)[CH2:4][C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 5234Sodium ChlorideHCID 70518003HCID 70518003, compound

Product 1

HCID 54367787HCID 54367787, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of methyl 3-methoxy-4-[(2R)-4-oxoazetidin-2-yl]but-2-enoate[(E,Z)-isomeric mixture](35 mg) in 1N hydrochloric acid (2 ml) was stirred at 25° C. for two hours. The resultant solution was saturated with sodium chloride and extracted three times with chloroform. The combined extracts were dried over magnesium sulfate and evaporated. The residue (29 mg) was chromatographed on silica gel (1.5 g) eluting with 2% methanol in dichloromethane to give methyl 3-oxo-4-[(2R)-4-oxoazetidin-2-yl]butanoate (28 mg), mp. 45.0°-46.5° C.:

Workup

  1. extractionextracted three times with chloroform
  2. dry with materialThe combined extracts were dried over magnesium sulfate
  3. customevaporated
  4. customThe residue (29 mg) was chromatographed on silica gel (1.5 g)
  5. washeluting with 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-487768edf4d24a358c4d35f3551d2fa7
Source dataset
uspto-grants-1985_09
Patent number
US04539152

Reaction notes

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