Ammonia → (S)-methyl-3-hydroxyglutaramate

Temperature

20.5 °C

Tert-pentanol (200 ml) was saturated with anhydrous ammonia at ambient pressure. This was cooled to ambient temperature and to this CaLB-T1-AMD enzyme (1.25 g) and dimethyl 3-hydroxyglutarate (25.3 g) were added. The resulting mixture was gently stirred with a magnetic stirrer at ambient temperature (20-21° C.) for 18 h. The enzyme was removed by filtration and washed with tert-pentanol (25 ml). The clear filtrate (200 g) was concentrated under reduced pressure at a maximum temperature of +50° C. to light brown oil. The oil was again dissolved in tert-pentanol (90 ml) and placed in a mechanically stirred 500 ml vessel. To this MTBE (Methyl tert-butyl ether) was slowly added under seeding with methyl (S)-3-hydroxyglutaramate (10 mg). The crystal suspension was cooled in an ice-bath to +5° C. The reaction mass was filtered, washed with MTBE and dried to yield (S)-methyl-3-hydroxyglutaramate.

1. additionwere added
2. customThe enzyme was removed by filtration
3. washwashed with tert-pentanol (25 ml)
4. concentrationThe clear filtrate (200 g) was concentrated under reduced pressure at a maximum temperature of +50° C.
5. dissolutionThe oil was again dissolved in tert-pentanol (90 ml)
6. additionTo this MTBE (Methyl tert-butyl ether) was slowly added
7. temperatureThe crystal suspension was cooled in an ice-bath to +5° C
8. filtrationThe reaction mass was filtered
9. washwashed with MTBE
10. customdried

ORD record

ord-d91b5dc796bc4b91a1e1f00d02ed9b74

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09273333B2