Z-Asp(OtBu)-Leu-OBzl → H-Asp(OtBu)-Leu-OH

HRID 1278534Notes

Reaction equation

HRID 1278534 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:11]([NH:13][C@H:14]([C:19]([O:21]CC1C=CC=CC=1)=[O:20])[CH2:15][CH:16]([CH3:18])[CH3:17])=[O:12])[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7]>CO.[Pd]>[NH2:1][C@H:2]([C:11]([NH:13][C@H:14]([C:19]([OH:21])=[O:20])[CH2:15][CH:16]([CH3:17])[CH3:18])=[O:12])[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7]

Participants

4

Reactant 1

HCID 131721133Z-Asp(OtBu)-Leu-OBzl

Product 1

HCID 131721134H-Asp(OtBu)-Leu-OHYield 89.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The Z-Asp(OtBu)-Leu-OBzl (15.6 g) in methanol (50 mL) was added 10% Pd on carbon (0.17 g) and was hydrogenated on a Paar Shaker. After filtering off the catalyst, the filtrate was concentrated to give a foamy solid. The crude product was triturated with diethyl ether to yield 8.03 g of H-Asp(OtBu)-Leu-OH.

Workup

  1. filtrationAfter filtering off the catalyst
  2. concentrationthe filtrate was concentrated
  3. customto give a foamy solid
  4. customThe crude product was triturated with diethyl ether

Sources & evidence

ORD record
ord-8a702763b56c4039b0f4fdbaa1414b89
Source dataset
uspto-grants-2002_09
Patent number
US06444457B1

Reaction notes

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