Triethylamine → HCID 53904920, compound

HRID 851382Notes

Reaction equation

HRID 851382 reaction equation
[O:1]=[C:2]1[NH:5][C@H:4]([CH2:6][CH:7]=[CH:8][C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:3]1.C(N(CC)CC)C.[C:26]([Si:30]([CH3:33])([CH3:32])Cl)([CH3:29])([CH3:28])[CH3:27]>CN(C)C=O.C(OCC)(=O)C>[Si:30]([N:5]1[C:2](=[O:1])[CH2:3][C@H:4]1[CH2:6][CH:7]=[CH:8][C:9]([O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:10])([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:33])[CH3:32]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 53759235HCID 53759235, compound

Product 1

HCID 53904920HCID 53904920, compoundYield 55.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of benzyl 4-[(2R)-4-oxoazetidin-2-yl]but-2-enoate (16 mg) and triethylamine (18 μl) in dimethylformamide (0.5 ml) was added tert-butyl-dimethylchlorosilane (15 mg) at 5° C. The mixture was stirred at the same temperature for one hour and at room temperature for 30 minutes. The resultant mixture was diluted with ethyl acetate (20 ml), washed with chilled dilute hydrochloric acid, a dilute aqueous sodium bicarbonate, and brine. Drying over magnesium sulfate and removal of the solvent left an oil (23 mg), which was chromatographed on a silica gel plate (developing solvent: 5% methanol in dichloromethane) to give benzyl 4-[(2R)-1-(tert-butyl-dimethylsilyl)-4-oxoazetidin-2-yl)but-2-enoate (13 mg).

Workup

  1. washwashed
  2. temperaturewith chilled dilute hydrochloric acid
  3. dry with materialDrying over magnesium sulfate and removal of the solvent
  4. waitleft an oil (23 mg), which
  5. customwas chromatographed on a silica gel plate (developing solvent: 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-ef5e6d15cec84bf99ae585a531a99801
Source dataset
uspto-grants-1983_05
Patent number
US04383945

Reaction notes

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