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161869-03-0

MOC-DIP synthesis

3synthesis methods
-

Yield:161869-03-0 83%

Reaction Conditions:

Stage #1: 1-[(methoxycarbonyl)oxy]pyrrolidine-2,5-dione;(S)-β,β-diphenyl-α-alaninewith sodium hydroxide;sodium carbonate in water at 20; for 2 h;
Stage #2: with hydrogenchloride in water;

Steps:

1.E

To a solution of L-diphenylalanine (241 mg, 1.0 mmol) (Peptech Corp.) in 5 mL IN NaOH and 0.5 mL saturated NaiCOs (resulting solution at pH 10) was added niethoxycarbonyloxysuccinimide (carbonic acid 2,5-dioxo-pyrrolidin-l-yl ester methyl ester) (180 mg, 1.1 mmol) dissolved in 5 mL. Afterwards, the reaction mixture was stirred at room temperature for 2 h. The alkaline solution was extracted once with ether (10 mL) and the aqueous phase was acidified with IN HC1. This was extracted twice with 20 mL EtOAc, and the combined organic phases were washed with 50 mL IN HC1. The organic phase was dried over NaaSO^ filtered and evaporated to an oil, which solidifies to yields 250 mg (83%) of the desired material. This derivative was used as such in the next step.

References:

WO2006/12725,2006,A1 Location in patent:Page/Page column 44