Potassium Carbonate → 3-(2-Chloro-5-nitro-phenoxymethyl)-azetidine-1-carboxylic acid tert-butyl ester

HRID 887666Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].C([O-])([O-])=O.[K+].[K+].[C:18]([O:22][C:23]([N:25]1[CH2:28][CH:27]([CH2:29]OS(C)(=O)=O)[CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19]>CN(C=O)C.CCOC(C)=O>[C:18]([O:22][C:23]([N:25]1[CH2:28][CH:27]([CH2:29][O:11][C:3]2[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=2[Cl:1])[CH2:26]1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

Conditions

Temperature: 50 °C

Procedure

To the mixture of 2-chloro-5-nitro-phenol (1.31 g, 7.54 mmol) and K2CO3 (1.57 g, 11.31 mmol) in 20 mL of DMF was added 3-methanesulfonyloxymethyl-azetidine-1-carboxylic acid tert-butyl ester (2.0 g, 7.54 mol). The reaction mixture was stirred at 50° C. for 1 h. After cooling to RT, the reaction mixture was diluted in 100 mL of EtOAc and quenched with 50 mL of water. The organic layer was separated and the aqueous layer was extracted with EtOAc (2×50 mL). The combined organic phases were washed with brine, dried over MgSO4 and concentrated in vacuum. The title compound was obtained via column chromatography (silica gel, 1;1 hexane/EtOAc) as yellow oil with 93% yield.

Workup

temperatureAfter cooling to RT
customquenched with 50 mL of water
customThe organic layer was separated
extractionthe aqueous layer was extracted with EtOAc (2×50 mL)
washThe combined organic phases were washed with brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuum

Sources & evidence

ORD record: ord-975cb70a78cd4cf3a70230c1d7aebc31
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247430B2

Reaction notes

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