Trifluoroacetic acid → HCID 10958749, compound

HRID 2187997Notes

Reaction equation

[C:1]([NH:4][CH:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2].[Na].C(=O)=O.C(#N)C.[N:23]([CH:26]1[CH2:30][C:29](=[O:31])[CH:28]=[CH:27]1)=[N+:24]=[N-:25].FC(F)(F)C(O)=O>C(O)C>[N:23]([C@H:26]1[C@H:27]([C:5]([NH:4][C:1]([CH3:2])=[O:3])([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:28][C:29](=[O:31])[CH2:30]1)=[N+:24]=[N-:25]

Participants

Conditions

Temperature: -40 °C

Procedure

To a solution of diethyl acetamidomalonate (Aldrich, 1.25 g, 5.7 mmol) in ethanol (10 mL) under nitrogen was added freshly cut sodium metal (0.03 g, 1.4 mmol). The reaction mixture was stirred at room temperature until all sodium has dissolved. The reaction mixture was cooled to −40° C. (dry ice/acetonitrile) and a solution of 4-azidocyclopent-2-enone (0.7 g, 5.7 mmol) in ethanol (5 mL) was added dropwise over a period of 10 min. The reaction mixture was stirred at −40° C. for 30 min and quenched with trifluoroacetic acid (0.1 mL, 1.4 mmol). The solvent was removed in vacuo to furnish a white solid. Purification of the crude by flash column chromatography (60% ether in hexane) gave 1.2 g (63%) of trans-3-azido-4-[(methylcarbonyl-amino)bis(ethoxycarbonyl)methyl]cyclopentanone as a white solid, mp 121-122° C.

Workup

dissolutionhas dissolved
customThe solvent was removed in vacuo
customto furnish a white solid
customPurification of the crude by flash column chromatography (60% ether in hexane)

Sources & evidence

ORD record: ord-736a47e533704cea8b365b24a8473edc
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06410594B1

Reaction notes

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