BocAsnGlyOBzl → HCID 129820428, compound

HRID 35814Notes

Reaction equation

HRID 35814 reaction equation
[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:2]([C:7]([NH:9][CH2:10][C:11]([O:13]CC1C=CC=CC=1)=[O:12])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5]>CO.[Pd]>[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:2]([C:7]([NH:9][CH2:10][C:11]([OH:13])=[O:12])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5]

Participants

4

Reactant 1

HCID 15602370BocAsnGlyOBzl

Product 1

HCID 129820428HCID 129820428, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The 64 g BocAsnGlyOBzl from above is dissolved in 500 ml MeOH and hydrogenated for 20 hours with 5 g 10% Pd-C as catalyst. The catalyst is removed by filtration and the solvent removed to give BocAsnGlyOH. This is dissolved in 200 ml DMF cooled to -20° C. and then activated with 20 g HoSu and 35 g DCC for 2 hours. 59 g BocGlyValOBzl is deBoced in HCl-EtAc, the HCl-EtAc removed by evaporation and the resulting oil taken up in 100 ml DMF and neutralized with 24 ml TEA. This is then added to the preactivated BocAsnGlyOSu. The mixture is stirred overnight, DCU removed by filtration and the DMF removed by evaporation. The residue is taken up in EtAc washed with sat. Nacl, sat. NaHCO3, and 10% citric acid. After drying the EtAc with MgSO4, it is removed by evaporation to give a powder, which is dried in a desiccator. Yield: 60 g (70%).

Workup

  1. customThe catalyst is removed by filtration
  2. customthe solvent removed

Sources & evidence

ORD record
ord-0dda4ccb452748029910b2401002435e
Source dataset
uspto-grants-1995_05
Patent number
US05411942

Reaction notes

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