Hydrochloric Acid → (2S,3S)-2-Chloro-3-methylvaleric Acid

To a cooled (0° C.) solution of L-Isoleucine (40 g) dissolved in HCl (5N, 750 ml) was added dropwise a solution of sodium nitrite (35 g in 100 ml water). The reaction was stirred overnight at room temperature (˜23° C.), Na2CO3 (31 g) slowly added and the reaction mixture extracted with EtOAc (3×150 ml). The combined organic extracts washed with water, half saturated brine, dried over MgSO4, filtered and concentrated. The product a yellowish oil was distilled under reduced pressure (5 torr, bp=111° C.) to afford a colorless oil (32 g) obtained in 70% yield. (see FIG. 6).

1. additionslowly added
2. extractionthe reaction mixture extracted with EtOAc (3×150 ml)
3. washThe combined organic extracts washed with water, half saturated brine
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. distillationThe product a yellowish oil was distilled under reduced pressure (5 torr, bp=111° C.)

ORD record

ord-6f4504ab3a8a4389ad4b7b8b30126e8f

Source dataset

uspto-grants-2002_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06417399B1