1-Piperazinecarboxylic acid, ethyl ester → HCID 15481710, compound

HRID 1859005Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]1([CH2:13][N:14]2[CH:18]=[N:17][CH:16]=[N:15]2)[C@H:11]([CH3:12])[O:10]1.[N:19]1([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]([OH:10])([C@H:11]([N:22]1[CH2:21][CH2:20][N:19]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:24][CH2:23]1)[CH3:12])[CH2:13][N:14]1[CH:18]=[N:17][CH:16]=[N:15]1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of (2R,3S)-2-(2,4-difluorophenyl)-3-methyl-2-(1H-1,2,4-triazol-1-yl)methyloxirane IV (1.0 g, 4.0 mmol), ethyl piperazine-1-carboxylate (1.2 ml, 8 mmol) and potassium carbonate in DMF (5 ml) was heated at 120° C. for 18 h. After cooling the reaction mixture was poured onto crushed ice and extracted with ethyl acetate (3×30 ml). The combined extract was washed with water, brine, dried (MgSO4) and concentrated and the resulting product was purified on a column of silica gel (hexane/EtOAc, 1:1) to give the title compound as off-white solid (400 mg, 24%).

Workup

temperatureAfter cooling the reaction mixture
additionwas poured
customonto crushed ice
extractionextracted with ethyl acetate (3×30 ml)
extractionThe combined extract
washwas washed with water, brine
dry with materialdried (MgSO4)
concentrationconcentrated
customthe resulting product was purified on a column of silica gel (hexane/EtOAc, 1:1)

Sources & evidence

ORD record: ord-2158ad69b13d406d9412a125a9482271
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06153616

Reaction notes

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