Potassium Carbonate → 2-(3-Cyano-benzyl)-1,1-dioxo-1lambda6-isothiazolidine-3-carboxylic acid methyl ester

HRID 1879470Notes

Reaction equation

[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][S:7](=[O:11])(=[O:10])[NH:6]1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[C:18]([C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23]Br)#[N:19].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][S:7](=[O:11])(=[O:10])[N:6]1[CH2:23][C:22]1[CH:25]=[CH:26][CH:27]=[C:20]([C:18]#[N:19])[CH:21]=1)=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 1,1-dioxo-1λ6-isothiazolidine-3-carboxylic acid methyl ester (Intermediate 1, 0.200 g, 1.10 mmol) in N,N-dimethylformamide (5 mL) was added potassium carbonate (0.450 g, 3.20 mmol) at room temperature under nitrogen. The reaction mixture was cooled to 0° C. and 3-cyano benzyl bromide (available from Aldrich; 0.240 g, 1.22 mmol) was added into the reaction mixture slowly and followed by the addition of tetra-n-butylammonium (0.025 g, 0.07 mmol). The reaction was completed in 5 h at room temperature as monitored by silica TLC. The reaction mixture was diluted with ethyl acetate (25 mL), washed with water (3×15 mL), dried over sodium sulfate and concentrated under reduced pressure to provide crude material, which was purified by silica gel column chromatography (100-200 mesh) using a gradient of 20-30% ethyl acetate/hexanes to give 2-(3-cyano-benzyl)-1,1-dioxo-1λ6-isothiazolidine-3-carboxylic acid methyl ester (0.170 g, 56%).

Workup

washwashed with water (3×15 mL)
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customto provide crude material, which
customwas purified by silica gel column chromatography (100-200 mesh)

Sources & evidence

ORD record: ord-f1bb53d9b02143dbbac2661018fb4e26
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314250B2

Reaction notes

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