1-[(tert-Butoxycarbonyl)methyl]-Nalpha-benzyloxycarbonyl-D-tryptophan → 1-[(tert-Butoxycarbonyl)methyl]-D-tryptophan

HRID 1108207Notes

Reaction equation

HRID 1108207 reaction equation
[C:1]([O:5][C:6]([CH2:8][N:9]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:11]([CH2:12][C@H:13]([C:25]([OH:27])=[O:26])[NH:14]C(OCC2C=CC=CC=2)=O)=[CH:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([CH2:8][N:9]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:11]([CH2:12][C@H:13]([C:25]([OH:27])=[O:26])[NH2:14])=[CH:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 538032101-[(tert-Butoxycarbonyl)methyl]-Nalpha-benzyloxycarbonyl-D-tryptophan

Product 1

HCID 541076191-[(tert-Butoxycarbonyl)methyl]-D-tryptophanYield 90.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The 136 g of product obtained in Step A are diluted with 1.5 liters of methanol and hydrogenated in the presence of 5 g of 10% Pd/C under an H2 pressure of 1.2 bars. After 12 hours of reaction at ambient temperature, the solution is filtered and then concentrated in vacuo. 87 g of the expected product are obtained in the form of a beige powder.

Workup

  1. customAfter 12 hours of reaction at ambient temperature
  2. filtrationthe solution is filtered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2f6baca858304bb2ae1a0e355888bf21
Source dataset
uspto-grants-2000_05
Patent number
US06066633

Reaction notes

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