Hydrochloric Acid → benzyl 4-[(2RS)-4-oxoazetidin-2-yl]but-2-enoate

HRID 1719289Notes

Reaction equation

HRID 1719289 reaction equation
[Si]([N:8]1[C:11](=[O:12])[CH2:10][CH:9]1[CH2:13][CH:14]=[CH:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])(C(C)(C)C)(C)C.Cl.C(=O)(O)[O-].[Na+]>CO>[O:12]=[C:11]1[NH:8][CH:9]([CH2:13][CH:14]=[CH:15][C:16]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:17])[CH2:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 53904921benzyl 4-[(2RS)-1-(tert-butyldimethylsilyl)-4-oxoazetidin-2-yl]but-2-enoate

Product 1

HCID 53759236benzyl 4-[(2RS)-4-oxoazetidin-2-yl]but-2-enoateYield 97.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of benzyl 4-[(2RS)-1-(tert-butyl-dimethylsilyl)-4-oxoazetidin-2-yl]but-2-enoate (45 mg) in methanol was added 1N hydrochloric acid (0.1 ml) at 0°. After stirring at room temperature for 2.5 hours, the reaction mixture was neutrallized to pH 7 with saturated aqueous sodium bicarbonate. The resultant solution was concentrated, taken up into ethyl acetate (15 ml), and washed in turn with water and brine. Drying over magnesium sulfate and removal of the solvent left an oil, which was chromatographed on a silica gel plate (developing solvent: 6% methanol in dichloromethane) to give benzyl 4-[(2RS)-4-oxoazetidin-2-yl]but-2-enoate (30 mg) as a crystalline solid.

Workup

  1. concentrationThe resultant solution was concentrated
  2. washwashed in turn with water and brine
  3. dry with materialDrying over magnesium sulfate and removal of the solvent
  4. waitleft an oil, which
  5. customwas chromatographed on a silica gel plate (developing solvent: 6% methanol in dichloromethane)

Sources & evidence

ORD record
ord-fd540fcfcb0f4b3581d1ed90e1865aca
Source dataset
uspto-grants-1985_09
Patent number
US04539152

Reaction notes

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