Cesium carbonate → HCID 89500559, compound

HRID 2178508Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1)#[N:2].CS(O[CH:15]1[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:16]1)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.[Cl-].[Na+].O>[C:1]([C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[O:9][CH:15]1[CH2:16][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18]1)#[N:2]

Participants

Conditions

Temperature: 80 °C

Procedure

3-cyanophenol (284 mg, 2.38 mmol, 1.2 eq) is added to a mixture of tert-butyl 3-[(methylsulfonyl)oxy]azetidine-1-carboxylate (500 mg, 1.99 mmol, 1 eq) and Cs2CO3 (2.27 g, 6.96 mmol, 3.5 eq) in DMF (20 ml). The reaction is heated overnight at 80° C., then cooled to room temperature. Brine (100 ml) is added and the mixture is extracted twice with diethyl ether. The combined organic phases are washed with brine, dried over MgSO4 and evaporated under reduced pressure. The residue is purified by basic reverse phase chromatography (gradient: acetonitrile/H2O/NH4OH from 50/50/0.1 to 80/20/0.1) to afford 262.4 mg of tert-butyl 3-(3-cyanophenoxy)azetidine-1-carboxylate a1-43.

Workup

temperaturecooled to room temperature
extractionthe mixture is extracted twice with diethyl ether
washThe combined organic phases are washed with brine
dry with materialdried over MgSO4
customevaporated under reduced pressure
customThe residue is purified by basic reverse phase chromatography (gradient: acetonitrile/H2O/NH4OH from 50/50/0.1 to 80/20/0.1)

Sources & evidence

ORD record: ord-6dc7a9825ebf4068bd7fa451f6ea03fc
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067930B2

Reaction notes

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