3-Hydroxyazetidine hydrochloride → HCID 71731671, compound

HRID 1425763Notes

Reaction equation

HRID 1425763 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24]Br)=[CH:20][C:19]=2[CH3:26])=[O:17])[C:11](=[O:27])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[OH:29][CH:30]1[CH2:33][NH:32][CH2:31]1>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][N:32]3[CH2:33][CH:30]([OH:29])[CH2:31]3)=[CH:20][C:19]=2[CH3:26])=[O:17])[C:11](=[O:27])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 27592903-Hydroxyazetidine hydrochlorideHCID 866955384-Benzyloxy-1-[2-(4-bromomethyl-2-methyl-phenyl)-2-oxo-ethyl]-1H-pyridin-2-one

Product 1

HCID 71731671HCID 71731671, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-benzyloxy-1-[2-(4-bromomethyl-2-methyl-phenyl)-2-oxo-ethyl]-1H-pyridin-2-one (preparation 1d, 72 mg, 0.17 mmol) in DMF (2 mL) is added 3-hydroxyazetidine hydrochloride (56 mg, 0.51 mmol). The reaction mixture is stirred for 30 min at room temperature. The mixture is purified via reverse phase HPLC chromatography (Gilson, Xbridge C18 5 μm, gradient 5%→90% acetonitrile in water+0.3% NH4OH, 120 mL/min).

Workup

  1. customThe mixture is purified via reverse phase HPLC chromatography (Gilson, Xbridge C18 5 μm, gradient 5%→90% acetonitrile in water+0.3% NH4OH, 120 mL/min)

Sources & evidence

ORD record
ord-ab37c6bf9df64d65aab2a6d36c6104a8
Source dataset
uspto-grants-2015_01
Patent number
US08933079B2

Reaction notes

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