Benzyl (isobutylcarbamoyl)glycinate → (Isobutylcarbamoyl)glycine

HRID 2284530Notes

Reaction equation

HRID 2284530 reaction equation
[CH2:1]([NH:5][C:6]([NH:8][CH2:9][C:10]([O:12]CC1C=CC=CC=1)=[O:11])=[O:7])[CH:2]([CH3:4])[CH3:3]>[Pd].C(O)(C)C>[CH2:1]([NH:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=[O:11])=[O:7])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 118021846Benzyl (isobutylcarbamoyl)glycinate

Product 1

HCID 16785937(Isobutylcarbamoyl)glycineYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

Charge benzyl 2-(isobutylcarbamoylamino)acetate (200 g; 98.1% assay), dry Pd/C (20 g; 10% w/w), and isopropyl alcohol (2000 ml) into an autoclave. Degas under vacuum and purge with hydrogen three times. Stir at 60° C. under 50-60 psi of H2 for 4 hours. Cool the mixture to 20-30° C. and filter through diatomaceous earth and concentrate the filtrate under reduced pressure at 45-50° C. to 1-2 Vol. Add acetonitrile (1000 ml) and concentrate under reduced pressure at 45-50° C. to 2-3 Vol. Cool the mixture to 5-10° C. and filter. Dry the cake under reduced pressure at 45-50° C. to give of 2-(isobutylcarbamoylamino)acetic acid (112 g; 95.2% assay; 82.5% yield).

Workup

  1. customDegas under vacuum
  2. custompurge with hydrogen three times
  3. temperatureCool the mixture to 20-30° C.
  4. filtrationfilter through diatomaceous earth
  5. concentrationconcentrate the filtrate under reduced pressure at 45-50° C. to 1-2 Vol.
  6. additionAdd acetonitrile (1000 ml)
  7. concentrationconcentrate under reduced pressure at 45-50° C. to 2-3 Vol.
  8. temperatureCool the mixture to 5-10° C.
  9. filtrationfilter
  10. customDry the cake under reduced pressure at 45-50° C.

Sources & evidence

ORD record
ord-324e382198a9487e84b99768f0056864
Source dataset
uspto-grants-2015_09
Patent number
US09145435B2

Reaction notes

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