HCID 86594241, compound → HCID 69545596, compound

HRID 1062686Notes

Reaction equation

HRID 1062686 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C@@H:4]1[CH2:8][CH:7]([N:9]=[N+]=[N-])[CH2:6][N:5]1[C:12](=[O:30])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:16]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:31])[C@@H:4]1[CH2:8][CH:7]([NH2:9])[CH2:6][N:5]1[C:12](=[O:30])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][NH:22][C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[CH:16]=1

Participants

4

Reactant 1

HCID 86594241HCID 86594241, compound

Product 1

HCID 69545596HCID 69545596, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4.7 g (10.9 mmol) of 4-azido-1-[3-(3-tert-butyloxycarbonylaminomethylphenyl)propionyl]proline methyl ester (starting compound A10) are dissolved in 70 ml of methanol and, after addition of 0.5 g of Pd/C (10%), hydrogenated. After the reaction is complete, the catalyst is filtered off with suction and the filtrate is concentrated in vacuo. Drying under high vacuum results in 3.8 g of the title compound as a colorless solidified foam. The mass spectrum shows the molecular peak MH+ at 406 Da.

Workup

  1. filtrationthe catalyst is filtered off with suction
  2. concentrationthe filtrate is concentrated in vacuo
  3. customDrying under high vacuum

Sources & evidence

ORD record
ord-09cff7c87016416d853483444671fe78
Source dataset
uspto-grants-2005_11
Patent number
US06962941B2

Reaction notes

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