Dichloromethane → HCID 69004179, compound

HRID 2102301Notes

Reaction equation

F[B-](F)(F)F.[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][NH:16][C:15](=[O:19])[CH:14]1[C:20]1[O:24][N:23]=[C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=2)[N:21]=1)=[O:12])([CH3:9])([CH3:8])[CH3:7].Cl[CH2:33]Cl>>[C:6]([O:10][C:11]([N:13]1[CH:14]([C:20]2[O:24][N:23]=[C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=3)[N:21]=2)[C:15]([O:19][CH3:33])=[N:16][CH2:17][CH2:18]1)=[O:12])([CH3:9])([CH3:7])[CH3:8]

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 26255Tetrafluoroborate

HCID 69006888HCID 69006888, compound

Product 1

HCID 69004179HCID 69004179, compoundYield 61%

Procedure

Trimethyloxoniuim tetrafluoroborate (169.4 mg, 1.15 mmol) was added to 2-[3-(3-chloro-phenyl)-[1,2,4]oxadiazol-5-yl]-3-oxo-piperazine-1-carboxylic acid tert-butyl ester (450 mg, 1.15 mmol) in dichloromethane (3 mL) under argon at room temperature and then stirred overnight. The reaction mixture was directly purified by flash chromatography on basic alumina using 30% ethyl acetate in hexanes to afford the titled compound (284.6 mg, 61%). 1H NMR (CDCl3) δ (ppm): 8.09 (m, 1H), 7.97 (m, 1H), 7.46 (m, 2H), 4.88 (m, 1H), 4.01 (m, 1H), 3.72 (s, 3H), 3.51 (m, 3H), 3.35 (m, 1H), 2.90 (m, 1H), 1.34 (m, 9H).

Workup

customThe reaction mixture was directly purified by flash chromatography on basic alumina using 30% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-64ef1d31c1ba49f796a4388b75dcae8f
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576077B2

Reaction notes

Loading…