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

HRID 851383Notes

Reaction equation

HRID 851383 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-butyldimethylsilyl)-4-oxoazetidin-2-yl]but-2-enoate (45 mg) in methanol was added 1 N 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-966800ca7b2d4e40ad476f1b342a8c9c
Source dataset
uspto-grants-1983_05
Patent number
US04383945

Reaction notes

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