Bromotrimethylsilane → HCID 57289203, compound

Participants

Reaction Steps

(S)-7-[[Ethoxy(4-phenylbutyl)phosphinyl]acetyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid, (2,2-dimethyl-1-oxopropoxy)methyl ester (2.7 g) in dichloromethane (dried over alumina) is treated with bromotrimethylsilane (1.2 ml) via syringe and the reaction mixture is stirred for 16 hours under argon. The solvent and excess bromotrimethylsilane is evaporated in vacuo and the residue is taken up in ethyl acetate and water and stirred for 15 minutes. The layers are separated and the ethyl acetate is washed with 5% potassium sulfate, water, brine dried (MgSO4) and evaporated. The 2.3 g of crude product is chromatographed on silica (75 g) eluting with dichloromethane/methanol/acetic acid (19/0.5/0.5). After stripping solvent 1.9 g of product is left as a glass.

Provenance & Evidence