Phenyl glycidyl ether → 5-cyclopropyl-1-(2-hydroxy-3-phenoxypropyl)-8-methoxy-2,3,5,6-tetrahydrobenzo[b][1,5]diazocin-4(1H)-one

HRID 1614894Notes

Reaction equation

[CH:1]1([N:4]2[C:11](=[O:12])[CH2:10][CH2:9][NH:8][C:7]3[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:6]=3[CH2:5]2)[CH2:3][CH2:2]1.FC(F)(F)S([O-])(=O)=O.[Mg+2].FC(F)(F)S([O-])(=O)=O.[O:36]([CH2:43][CH:44]1[CH2:46][O:45]1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(=O)(O)[O-].[Na+]>C(#N)C>[CH:1]1([N:4]2[C:11](=[O:12])[CH2:10][CH2:9][N:8]([CH2:46][CH:44]([OH:45])[CH2:43][O:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:7]3[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:6]=3[CH2:5]2)[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 75 °C

Procedure

To a mixture of 5-cyclopropyl-8-methoxy-2,3,5,6-tetrahydrobenzo[b][1,5]diazocin-4(1H)-one (50.0 mg, 0.203 mmol) from Example 1 and magnesium trifluoromethanesulfonate (32.7 mg, 0.102 mmol) in acetonitrile (1.5 ml) was added 2-(phenoxymethyl)oxirane (30.5 mg, 0.203 mmol) and the resulting mixture was stirred at 75° C. for 100 hours. After cooling to room temperature was added sodium bicarbonate (saturated aqueous) and the mixture was extracted with dichloromethane. The organic phases were filtered through a pad of sodium sulfate and the filtrate evaporated. Preparative thin layer chromatography (EtOAc/MeOH: 95/5) of the obtained residue, gave the desired compound as a brown oil (52 mg, 65%).

Workup

temperatureAfter cooling to room temperature
extractionthe mixture was extracted with dichloromethane
filtrationThe organic phases were filtered through a pad of sodium sulfate
customthe filtrate evaporated

Sources & evidence

ORD record: ord-35d9f80dfc074e46bceecf40ee635e71
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765728B2

Reaction notes

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