HCID 86591771, compound → HCID 69545606, compound

HRID 1062684Notes

Reaction equation

HRID 1062684 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][C:18]([CH2:21][NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:17][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][C:18]([CH2:21][NH:22][C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])=[CH:17][CH:16]=1

Participants

4

Reactant 1

HCID 86591771HCID 86591771, compound2×

Product 1

HCID 69545606HCID 69545606, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

6.27 g (14.5 mmol) of 4-azido-1-[3-(4-tert-butyloxycarbonylaminomethylphenyl)propionyl]proline methyl ester (starting compound A5) are dissolved in 200 ml of methanol and, after addition of 0.6 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 5.47 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-34db1606773741a6bf27ce2e228583ca
Source dataset
uspto-grants-2005_11
Patent number
US06962941B2

Reaction notes

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