4-bromo-5H-furan-2-one → (S)-4-(1-{4-[3-(4-Ethoxy-phenoxy)-azetidin-1-yl]-phenyl}-ethylamino)-5H-furan-2-one

HRID 40515Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:23]=[CH:22][C:7]([O:8][CH:9]2[CH2:12][N:11]([C:13]3[CH:18]=[CH:17][C:16]([C@@H:19]([NH2:21])[CH3:20])=[CH:15][CH:14]=3)[CH2:10]2)=[CH:6][CH:5]=1)[CH3:2].Br[C:25]1[CH2:29][O:28][C:27](=[O:30])[CH:26]=1>C1COCC1>[CH2:1]([O:3][C:4]1[CH:23]=[CH:22][C:7]([O:8][CH:9]2[CH2:10][N:11]([C:13]3[CH:18]=[CH:17][C:16]([C@@H:19]([NH:21][C:25]4[CH2:29][O:28][C:27](=[O:30])[CH:26]=4)[CH3:20])=[CH:15][CH:14]=3)[CH2:12]2)=[CH:6][CH:5]=1)[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To 0.040 g (0.13 mmol) (S)-1-{4-[3-(4-ethoxy-phenoxy)-azetidin-1-yl]-phenyl}-ethylamine (X.1) in 1.5 mL THF are added 54 μL (0.38 mmol) TEA and 0.021 g (0.13 mmol) 4-bromo-2(5H)-furanone. The mixture is stirred for 12 h at 80° C. After concentration in vacuo the residue is purified by HPLC (SunfireC18, MeOH/water (+0.3% formic acid)) to yield the desired product.

Workup

concentrationAfter concentration in vacuo the residue
customis purified by HPLC (SunfireC18, MeOH/water (+0.3% formic acid))

Sources & evidence

ORD record: ord-243fb9227e5748ceb7e111f96df85aa7
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530461B2

Reaction notes

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