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ChemicalBook CAS DataBase List 3,3`-Dithiobispropanoic acid bis(N-hydroxysucciniMde ester)
57757-57-0

3,3`-Dithiobispropanoic acid bis(N-hydroxysucciniMde ester) synthesis

3synthesis methods
-

Yield: 85%

Reaction Conditions:

with 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in dichloromethane at 20; for 2 h;

Steps:

2.3. Compound 2
To the solution of 3,3'-dithioldipropionic acid (1 g, 4.75 mmol) in dichloromethane (20 mL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) (2.16 g, 10.5 mmol) and N-hydroxysuccinimide (1.21 g, 10.5 mmol) were added. The mixture was stirred for 2 h at room temperature. The solution was concentrated in vacuo, and the obtained residue was subjected to silica column chromatography (ethyl acetate/hexane = 1:5) to give the NHS ester 2 (1.63 g, 85%). 1H NMR (DMSO-d6, 400 MHz) δ 3.16 (m, 8H), 2.82 (s, 8H). FAB (DMSO-d6) [(M+H)+] calcd 405, found 405.

References:

Tanaka, Kazuo;Kitamura, Narufumi;Chujo, Yoshiki [Bioorganic and Medicinal Chemistry,2012,vol. 20,# 1,p. 96 - 100] Location in patent:experimental part

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