Triethylamine → HCID 86741964, compound

HRID 2413711Notes

Reaction equation

[N:1]([C@H:4]1[C:7](=[O:8])[NH:6][C@H:5]1[C:9]([O:11][CH3:12])=[O:10])=[N+]=[N-].[OH2:13].[C:14]1([CH3:24])C=CC(S(O)(=O)=O)=CC=1.[H][H].C(N(CC)CC)C>CN(C=O)C.C(Cl)Cl.[Pd]>[C:14]([NH:1][C@H:4]1[C:7](=[O:8])[NH:6][C@H:5]1[C:9]([O:11][CH3:12])=[O:10])(=[O:13])[CH3:24]

Participants

Conditions

Temperature: -10 °C

Procedure

In 50 ml of DMF were dissolved 1.67 g of methyl (±)cis-3-azido-4-oxo-2-azetidinecarboxylate (29) and 1.86 g of p-toluenesulfonic acid monohydrate and, 400 mg of 10% Pd-C was added to the solution followed by hydrogenation at ambient temperature under atmospheric pressure of hydrogen. The catalyst was filtered off and the solvent was removed by distillation under reduced pressure to obtain a viscous oil. The oil was dissolved in 80 ml of methylene chloride. The solution was cooled to -10° C. and, 2.89 ml of triethylamine and 0.736 ml of acetyl chdloride were added to the solution in sequence. The mixture was stirred at the same temperature for 1 hour and 20 minutes. The reaction mixture was concentrated under reduced pressure and the residue was subjected to column chromatography using 100 g of silica gel. By eluting with ethyl acetate-methanol (10:1), 683 mg of methyl (±)cis-3-acetylamino-4-oxo-2-azetidinecarboxylate (31) was obtained as a white solid.

Workup

additionwas added to the solution
filtrationThe catalyst was filtered off
customthe solvent was removed by distillation under reduced pressure
customto obtain a viscous oil
concentrationThe reaction mixture was concentrated under reduced pressure
washBy eluting with ethyl acetate-methanol (10:1)

Sources & evidence

ORD record: ord-6aeb695831bf4ffd9bd97707fc4fa09c
Source dataset: uspto-grants-1988_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04719207

Reaction notes

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