Npc316347 → Methyl (3Z)-2-[(tert-butoxycarbonyl)amino]-5-cyano-2-methylpent-3-enoate

3-Cyanobutyltriphenylphosphonium bromide (0.990 g, 0.0025 mol) is taken up in dry THF (30 mL) and purged with argon. To this sodium is added bis(trimethylsilyl)amide (3 mL 1.0M solution in THF, 0.003 mol) at 20° C. to 25° C. and the reaction mixture is stirred at this temperature for 10 min. After a yellow color change is observed, a solution of the methyl 2-[(tert-butoxycarbonyl)amino]-2-methyl-3-oxopropanoate product of Example 1c (578 mg, 0.0025 mol) in THF (20 mL) is then added and the reaction mixture is stirred under argon for 8 h at 25° C. It is then concentrated on rotovap and the residual mass is taken up in EtOAc (100 mL) and washed with DI water (20 mL). The organic layer is dried over anhydrous MgSO4, decolorized with activated charcoal (1.0 g), filtered through Celite and concentrated on a rotovap to give crude reaction product as a dark brown oil. Column chromatography of this crude product affords the desired title product.

1. custompurged with argon
2. stirringthe reaction mixture is stirred under argon for 8 h at 25° C
3. concentrationIt is then concentrated on rotovap
4. washwashed with DI water (20 mL)
5. dry with materialThe organic layer is dried over anhydrous MgSO4
6. filtrationfiltered through Celite
7. concentrationconcentrated on a rotovap
8. customto give crude
9. customreaction product as a dark brown oil

ORD record

ord-11fbef605922483094bbda30c33ca977

Source dataset

uspto-grants-2004_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06828456B2