Triethylamine → O-(2-diazo-1,3-dioxobutyl)-N-trifloroacetyl-L-serine

HRID 2165240Notes

Reaction equation

[C:1]([O:7][CH2:8][C@@H:9]([C:17]([OH:19])=[O:18])[NH:10][C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].C(N(CC)CC)C.C1(C)C=CC(S([N:36]=[N+:37]=[N-])(=O)=O)=CC=1>C(O)C>[N+:36](=[C:2]([C:3](=[O:4])[CH3:5])[C:1]([O:7][CH2:8][C@@H:9]([C:17]([OH:19])=[O:18])[NH:10][C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])=[O:6])=[N-:37]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of O-acetoacetyl-N-trifluoroacetyl-L-serine (232 mg) and triethylamine (0.41 ml) in ethanol (7 ml) was added p-toluenesulfonyl azide (193 mg) at 0° C. The mixture was stirred for an hour at 0° C. and for 4 hours at room temperature. The solvent was distilled off in vacuo and the residue was diluted with chloroform and washed successively with aqueous acetic acid, water and brine. After drying over sodium sulfate, the chloroform extract was filtered and concentrated. The residue was flash chromatographed on silica gel (10 g) eluting successively with chloroform and a 1:9 mixture of methanol and chloroform to give O-(2-diazo-1,3-dioxobutyl)-N-trifloroacetyl-L-serine (193 mg).

Workup

distillationThe solvent was distilled off in vacuo
additionthe residue was diluted with chloroform
washwashed successively with aqueous acetic acid, water and brine
dry with materialAfter drying over sodium sulfate
extractionthe chloroform extract
filtrationwas filtered
concentrationconcentrated
customchromatographed on silica gel (10 g)
washeluting successively with chloroform
additiona 1:9 mixture of methanol and chloroform

Sources & evidence

ORD record: ord-0f77168854cc4cc39edeae367afea197
Source dataset: uspto-grants-1990_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04939241

Reaction notes

Loading…