HCID 14720887, compound → HCID 13454828, compound

HRID 1722485Notes

Reaction equation

HRID 1722485 reaction equation
[CH:1]([NH:4][C:5](=[O:11])[CH:6]([N:8]=[N+]=[N-])[CH3:7])([CH3:3])[CH3:2]>[Ni].C(O)(C)C>[CH:1]([NH:4][C:5](=[O:11])[C@@H:6]([CH3:7])[NH2:8])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 14720887HCID 14720887, compound

Product 1

HCID 13454828HCID 13454828, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 3776IsopropanolSolvent

Procedure

A 14.3 g sample of (R)-ethyl-2-azidopropionate was taken up in 50 mL of isopropylamine and allowed to stand for 24 hours. After stripping excess amine, 14.8 g of pure N-isopropyl-2-azidopropionamide was obtained. The amide thus obtained, 3.12 g, was stirred with 5.0 g of Raney nickel catalyst in 40 mL of isopropanol until nitrogen evolution ceased. The solution was filtered and concentrated in vacuo at 40° C. to give 2.5 g of crude N-isopropyl-D-alanine amide.

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated in vacuo at 40° C.

Sources & evidence

ORD record
ord-f5ecbc25551f4b21a242dd5cd178749b
Source dataset
uspto-grants-1989_08
Patent number
US04855455

Reaction notes

Loading…