Hydrochloric Acid → HCID 58280475, compound

HRID 1879471Notes

Reaction equation

C[O:2][C:3]([CH:5]1[CH2:9][CH2:8][S:7](=[O:11])(=[O:10])[N:6]1[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]#[N:20])[CH:14]=1)=[O:4].O.[OH-].[Li+].Cl>O1CCCC1.O>[C:19]([C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[CH2:12][N:6]1[CH:5]([C:3]([OH:4])=[O:2])[CH2:9][CH2:8][S:7]1(=[O:10])=[O:11])#[N:20]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 2-(3-cyano-benzyl)-1,1-dioxo-1λ6-isothiazolidine-3-carboxylic acid methyl ester (6.0 g, 20.4 mmol) in a tetrahydrofuran-water mixture (4:1, 50 mL), lithium hydroxide monohydrate (2.5 g, 59.6 mmol) was added at room temperature and stirred at this temperature for 4 h. Then tetrahydrofuran was removed from the reaction mixture under reduced pressure. The residual reaction mixture was cooled to 0° C. and 1N hydrochloric acid was added to make the pH˜2. The acidified reaction mixture was extracted with ethyl acetate (3×150 mL). The combined organic layers were washed with water (2×50 mL) followed by brine (50 mL) and then dried over sodium sulfate and concentrated under reduced pressure to provide 2-(3-cyano-benzyl)-1,1-dioxo-1λ6-isothiazolidine-3-carboxylic acid (5.2 g, 91%).

Workup

customThen tetrahydrofuran was removed from the reaction mixture under reduced pressure
customThe residual reaction mixture
customThe acidified reaction mixture
extractionwas extracted with ethyl acetate (3×150 mL)
washThe combined organic layers were washed with water (2×50 mL)
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-baf0ffd7f56c4a248097e591e7bfd8c7
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314250B2

Reaction notes

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