HCID 86591771, compound → HCID 69545606, compound

HRID 583951Notes

Reaction equation

HRID 583951 reaction equation
[N:1]([CH:4]1[CH2:8][N:7]([C:9](=[O:27])[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:14][CH:13]=2)[C@H:6]([C:28]([O:30][CH3:31])=[O:29])[CH2:5]1)=[N+]=[N-]>CO.[Pd]>[NH2:1][CH:4]1[CH2:8][N:7]([C:9](=[O:27])[CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([CH2:18][NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:24])[CH3:25])=[O:21])=[CH:16][CH:17]=2)[C@H:6]([C:28]([O:30][CH3:31])=[O:29])[CH2:5]1

Participants

4

Reactant 1

HCID 86591771HCID 86591771, compound2×

Product 1

HCID 69545606HCID 69545606, compoundYield 92.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

6.27 g of methyl 4-azido-1-[3-(4-tert-butyloxycarbonylaminomethylphenyl)propionyl]prolinate (starting material A5) are dissolved in 200 ml of methanol and, after addition of 0.6 g of Pd/C (10%), hydrogenated. After the reaction has ended, the catalyst is filtered off with suction and the filtrate is concentrated under reduced pressure. Drying under high vacuum gives 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 under reduced pressure
  3. customDrying under high vacuum

Sources & evidence

ORD record
ord-b50e2c495a8845889131966676d8983f
Source dataset
uspto-grants-2005_08
Patent number
US06924305B2

Reaction notes

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