Methanol → HCID 22723509, compound

To the reaction mixture obtained by the method of Example 2 were added 10% aqueous sodium hydroxide solution (113.8 g) and methanol (20 mL), and the mixture was stirred overnight at room temperature. The disappearance of tert-butyl 4-cyano-3-hydroxy-4-methylpentanoate was confirmed by GC. Toluene (50 mL) was added, and the mixture was stirred and then partitioned to remove the toluene layer. 20% Aqueous hydrochloric acid solution (67.5 g) was added to the aqueous layer to adjust its pH to an acidic one (ca. 1-2), and the mixture was extracted twice with a mixed solution (150 mL) of ethyl acetate-n-butanol (1:1). The layer of the mixed solution was concentrated under reduced pressure to give 4-cyano-3-hydroxy-4-methylpentanoic acid (18.75 g) as an oil. The yield was 84% relative to tert-butyl 4-cyano-3-hydroxy-4-methylpentanoate, but crystallization did not occur.

1. customTo the reaction mixture obtained by the method of Example 2
2. stirringthe mixture was stirred
3. custompartitioned
4. customto remove the toluene layer
5. addition20% Aqueous hydrochloric acid solution (67.5 g) was added to the aqueous layer
6. extractionthe mixture was extracted twice with a mixed solution (150 mL) of ethyl acetate-n-butanol (1:1)
7. concentrationThe layer of the mixed solution was concentrated under reduced pressure

ORD record

ord-6e46dfba9bd54a11891b000bc49f29c9

Source dataset

uspto-grants-2004_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06730803B2