Hydrochloric Acid → HCID 14503313, compound

To a solution containing 3-(S)-[(benzyloxycarbonyl)amino]-2-acetoxy-4-methylpentanenitrile (see example 1 of WO 96/16080) (15.2 g, 50.0 mmol) in 183 mL of dioxane was added 183 mL of concentrated hydrochloric acid and 7.45 mL of anisole. The reaction mixture was heated to reflux overnight. The hydrolysis reaction was allowed to cool to room temperature and then concentrated in vacuo. The resulting aqueous solution was extracted with ether (2X). The aqueous phase was placed on a Dowex 50X8-100 column (H+ form, preeluted with deionized water to pH=7). The column was eluted with 2.0 N ammonium hydroxide and the pure fractions concentrated to afford 5.53 g (75%) of 3-(S)-amino-2-(R,S)-hydroxy-4-methylpentanoic acid as a pale yellow solid. FAB MS [M+H] m/z; Calcd: 148, Found: 148.

1. temperatureThe reaction mixture was heated
2. temperatureto reflux overnight
3. customThe hydrolysis reaction
4. concentrationconcentrated in vacuo
5. extractionThe resulting aqueous solution was extracted with ether (2X)
6. washThe column was eluted with 2.0 N ammonium hydroxide
7. concentrationthe pure fractions concentrated

ORD record

ord-cb830978b3e14ad6923cc9049f87e7f7

Source dataset

uspto-grants-2000_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06150334