Water → HCID 21990153, compound

HRID 2377169Notes

Reaction equation

[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][C:15]([N:17]3[CH2:20][CH:19]([OH:21])[CH2:18]3)=[O:16])=[CH:9][C:4]=2[CH:3]=[CH:2]1.C(N(CC)C(C)C)(C)C.[CH3:31][O:32][CH2:33]Cl.O>C(Cl)Cl.C(OCC)(=O)C>[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][C:15]([N:17]3[CH2:20][CH:19]([O:21][CH2:31][O:32][CH3:33])[CH2:18]3)=[O:16])=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

Conditions

Temperature: 5 °C

Procedure

In 8.5 mL of methylene chloride was dissolved 1.52 g of 3-[2-(1-benzothiophen-5-yl)ethoxy]-1-(3-hydroxy-1-azetidinyl)-1-propanone, and 2.6 mL of N,N-diisopropylethyl-amine was added to the solution. After the resulting mixture was cooled to 5° C., 1.0 mL of chloromethyl methyl ether was added thereto, followed by stirring at room temperature for 17 hours. Water and ethyl acetate were added to the reaction mixture and the organic layer was separated. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent. The residue was purified by a column chromatography (eluent; toluene:ethyl acetate=3:1 to 1:1) to obtain 1.40 g of 3-[2-(1-benzothiophen-5-yl)ethoxy]-1-[3-(methoxymethoxy)-1-azetidinyl]-1-propanone as an oil.

Workup

additionwas added to the solution
customthe organic layer was separated
washThe organic layer was washed with a saturated aqueous sodium chloride solution
dry with materialdried over anhydrous magnesium sulfate
distillationdistilled under reduced pressure
customto remove the solvent
customThe residue was purified by a column chromatography (eluent; toluene:ethyl acetate=3:1 to 1:1)

Sources & evidence

ORD record: ord-0cfeeb7fea644d12aee4b23805c2a6ef
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07468443B2

Reaction notes

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