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ChemicalBook CAS DataBase List Z-VAL-OSU
3496-11-5

Z-VAL-OSU synthesis

5synthesis methods
N-Hydroxysuccinimide

6066-82-6

N-Carbobenzyloxy-L-valine

1149-26-4

Z-VAL-OSU

3496-11-5

Step 1. To a stirred solution of N-hydroxybutanediimide (1 g, 4 mmol) and CBZ-L-valine (459 mg, 4 mmol) in tetrahydrofuran (THF, 20 mL) was added N,N'-dicyclohexylcarbodiimide (DCC, 908 mg, 4.4 mmol) at 0° C. The reaction was carried out at room temperature. The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the mixture was filtered and the filtrate was concentrated to afford (S)-2,5-dioxopyrrolidin-1-yl 2-(((benzyloxy)carbonyl)amino)-3-methylbutanoate (yield: 90%).

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Yield:-

Steps:

Multi-step reaction with 2 steps
1: sodium carbonate / water / 16 h / 28 °C
2: dicyclohexyl-carbodiimide / tetrahydrofuran / 16 h / 0 - 20 °C

References:

GENENTECH, INC.;THE UNIVERSITY OF AUCKLAND;LEE, Ho Huat;TERCEL, Moana;FLYGARE, John A.;GUNZNER-TOSTE, Janet;PILLOW, Thomas H.;SAFINA, Brian;STABEN, Leanna;VERMA, Vishal;WEI, BinQing;ZHAO, Guiling WO2015/95227, 2015, A2

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