Triethylamine → 1-(1(S)-t-butoxycarbonylethyl)-3(R)-azido-4(S)-phenylazetidin-2-one
Reaction equation
[CH:1](=[N:8][C@H:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[N:25]([CH2:28][C:29](Cl)=[O:30])=[N+:26]=[N-:27]>C(Cl)Cl>[C:14]([O:13][C:11]([C@@H:9]([N:8]1[C@@H:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C@@H:28]([N:25]=[N+:26]=[N-:27])[C:29]1=[O:30])[CH3:10])=[O:12])([CH3:16])([CH3:15])[CH3:17]Participants
Procedure
To 75 ml. of a solution of N-benzylidene-1(S)-t-butoxycarbonylethylamine (5.07 g., 21.7 mmol) and triethylamine (4.84 g., 47.8 mmol) in methylene chloride, there was gradually added dropwise 75 ml. of a solution of azidoacetyl chloride (5.19 g., 43.5 mmol) in methylene chloride at -78° C. After stirring at -78° C. to room temperature for 14 hours, the reaction mixture was washed with water and then with a saturated saline solution, followed by drying over anhydrous magnesium sulfate. After removal of the solvent by distillation, the residue was subjected to silica gel column chromatography, using hexane-ethyl acetate (3:1) as an eluent, to give 1-(1(S)-t-butoxycarbonylethyl)-3(S)-azido-4(R)-azetidin-2-one (2.68 g., yield: 39%) and 1-(1(S)-t-butoxycarbonylethyl)-3(R)-azido-4(S)-phenylazetidin-2-one (2.82 g., yield: 41%).
Workup
- customat -78° C
- washthe reaction mixture was washed with water
- dry with materialby drying over anhydrous magnesium sulfate
- customAfter removal of the solvent
- distillationby distillation
Sources & evidence
- ORD record
- ord-ae52efa7081f4c259857b11a5d8a0536
- Source dataset
- uspto-grants-1982_10
- Patent number
- US04352752
Reaction notes
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