Triethylamine → HCID 57305915, compound

HRID 1075640Notes

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([OH:16])=O)[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC)=O.[NH2:30][C@H:31]1[C@H:34]([O:35][C:36](=[O:38])[CH3:37])[NH:33][C:32]1=[O:39]>ClCCl.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([NH:30][C@H:31]1[C@H:34]([O:35][C:36](=[O:38])[CH3:37])[NH:33][C:32]1=[O:39])=[O:16])[CH3:13])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -2.5 °C

Procedure

To a solution of N-benzyloxycarbonyl-L-alanine (1.604 g, 7.188 mmole) and triethylamine (799 mg, 7.91 mmole) in dichloromethane (30 ml), ethyl chloroformate (738 mg, 6.83 mmole) was added at -15° C. The reaction mixture was stirred at -10 to 5° C. for 1.5 hrs. Then a precooled (ca. -15° C.) solution of (3S,4S)-3-amino-4-acetoxy-azetidin-2-one in ethyl acetate (see above) was added at -15° C. and the resulting mixture was stirred at 0° C. to room temperature for 2 hrs. After removal of solvent, the residue was dissolved in ethyl acetate, washed with cold saturated NaHCO3 solution, water, brine and dried over sodium sulfate. After removal of solvent, the residue was recrystallized from dichloromethane and (3S,4S)-3-(N-benzyloxycarbonyl-L-alanyl) amino-4-acetoxy-azetidin-2-one was obtained (1.36 g, 54% yield).

Workup

stirringthe resulting mixture was stirred at 0° C. to room temperature for 2 hrs
customAfter removal of solvent
dissolutionthe residue was dissolved in ethyl acetate
washwashed with cold saturated NaHCO3 solution, water, brine
dry with materialdried over sodium sulfate
customAfter removal of solvent
customthe residue was recrystallized from dichloromethane

Sources & evidence

ORD record: ord-e24e7640b99e4037af6daf6f2436b3b7
Source dataset: uspto-grants-1999_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05905076

Reaction notes

Loading…