HCID 117608159, compound → HCID 117608156, compound

HRID 58826Notes

Reaction equation

HRID 58826 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][CH:15]([CH2:20][C:21]#[N:22])[C:16]([O:18][CH3:19])=[O:17])[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CC(O)=O.[Pd]>[NH2:22][CH2:21][CH2:20][CH:15]([CH2:14][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:10]([O:12][CH3:13])=[O:11])[C:16]([O:18][CH3:19])=[O:17]

Participants

4

Reactant 1

HCID 117608159HCID 117608159, compound

Product 1

HCID 117608156HCID 117608156, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of (2S)-dimethyl 2-((tert-butoxycarbonyl)amino)-4-(cyanomethyl)pentanedioate (10.0 g, 31.8 mmol) in AcOH (240 mL) was added 10% Pd/C (2.0 g) and the mixture was stirred under H2 atmosphere (70 psi) for 3 h. The mixture was filtered through a pad of Celite and the filtrate was evaporated under reduced pressure. The residue was treated with MTBE and evaporated again to afford (4S)-dimethyl 2-(2-aminoethyl)-4-((tert-butoxycarbonyl)amino)pentanedioate (crude) as a light pink solid.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. customthe filtrate was evaporated under reduced pressure
  3. additionThe residue was treated with MTBE
  4. customevaporated again

Sources & evidence

ORD record
ord-d94b408e53a44352a3f772e60a7cbba4
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

Loading…