Potassium Carbonate → (5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzylsulfanyl)-acetic acid methyl ester

HRID 11692

Reaction equation

[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][CH2:7][C:8]([N:10]2[CH2:15][C@H:14]([CH3:16])[N:13]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH2:12][C@H:11]2[CH3:25])=[O:9])=[C:4]([CH2:28]Cl)[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:36]([O:40][CH3:41])(=[O:39])[CH2:37][SH:38]>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[CH3:41][O:40][C:36](=[O:39])[CH2:37][S:38][CH2:28][C:4]1[CH:3]=[C:2]([Cl:1])[CH:27]=[CH:26][C:5]=1[O:6][CH2:7][C:8]([N:10]1[CH2:15][C@H:14]([CH3:16])[N:13]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[CH2:12][C@H:11]1[CH3:25])=[O:9]

Participants

Conditions

Temperature: 50 °C

Procedure

To 2-(4-chloro-2-chloromethyl-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone (0.10 g, 0.23 mmol) in dimethyl formamide (2 ml) was added potassium carbonate (0.070 g, 0.51 mmol), tetrabutylammonium iodide (0.088 mg, 0.24 mmol) and finally methyl thioglycolate (0.02 ml, 0.25 mmol). The reaction was stirred at 50° C. for 19 hours. The reaction was diluted with ethyl acetate and washed with pH 7 phosphate buffer (0.05 M) and aqueous saturated sodium chloride. The organic layer was dried over magnesium sulfate and the title compound was isolated by chromatography on silica gel (0.046 g).

Workup

washwashed with pH 7 phosphate buffer (0.05 M) and aqueous saturated sodium chloride
dry with materialThe organic layer was dried over magnesium sulfate

Sources & evidence

ORD record: ord-9761802317cd43b78bc46201bd46de50
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07098212B2

Linked notes

Loading…