Methyl propiolate → 4-(Methoxycarbonyl)-alpha-methyl-1H-1,2,3-triazole-1-acetic acid

HRID 1888182Notes

Reaction equation

[C:1]([O:5][CH3:6])(=[O:4])[C:2]#[CH:3].[N:7]([CH:10]([CH3:18])[C:11]([O:13]C(C)(C)C)=[O:12])=[N+:8]=[N-:9]>C1(C)C=CC=CC=1>[CH3:6][O:5][C:1]([C:2]1[N:9]=[N:8][N:7]([CH:10]([CH3:18])[C:11]([OH:13])=[O:12])[CH:3]=1)=[O:4]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 1.87 g (22.3 mmol) of methyl prop-2-ynoate in 40 mL of toluene was added 1.9 g (11 mmol) of tert-butyl 2-azidopropanate. The reaction mixture was heated at 100° C. for 3 h then cooled to ambient temperature. All volatiles were removed under reduced pressure and the crude residue purified by column chromatography on silica gel eluting with a 5 to 25% acetone in hexanes gradient to afford the title compounds.

Workup

temperaturethen cooled to ambient temperature
customAll volatiles were removed under reduced pressure
customthe crude residue purified by column chromatography on silica gel eluting with a 5 to 25% acetone in hexanes gradient

Sources & evidence

ORD record: ord-1606d64436784ef086ccf7829821f77a
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501786B2

Reaction notes

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