Diethyl Ether → 2,3-Dihydroxybutanedioate

Participants

Reaction Steps

One batch of freebase (S)-2-Dimethylamino-N-(6-oxo-2-phenyl-5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indol-8-yl)-3-phenyl-propionamide (22 mg, 0.049 mmol) from Example 71a was triturated with 1:1 diethyl ether:hexane giving purified material (20 mg, 0.044 mmol). A portion (10 mg, 0.022 mmol) was then dissolved in a small amount of c.a. 1:1 tetrahydrofuran:methanol and treated with L-tartaric acid (3.3 mg, 0.022 mmol). The volatile components of the resulting clear solution were removed under a stream of argon. To the resulting yellow oil was added diethyl ether plus one drop of methanol giving a fine yellow precipitate which was isolated by decanting most of the liquid and subsequent high vacuum removal of the remaining volatile components to afford the title compound as a tartrate salt (13 mg, 0.022 mmol) in quantitative yield.

Provenance & Evidence