HCID 22942179, compound → HCID 22942182, compound

HRID 361963Notes

Reaction equation

HRID 361963 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][NH:8][C:9](=[O:26])[C@H:10]([C:22]([CH3:25])([CH3:24])[CH3:23])[NH:11]C(OCC1C=CC=CC=1)=O>C(O)C.[Pd]>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][NH:8][C:9](=[O:26])[C@H:10]([C:22]([CH3:24])([CH3:23])[CH3:25])[NH2:11]

Participants

4

Reactant 1

HCID 22942179HCID 22942179, compound

Product 1

HCID 22942182HCID 22942182, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

Cbz-L-tert-leucine-N-2-(2-methoxyethoxy)ethylamide (7.66 g, 20.9 mmol) was dissolved in ethanol (100 ml) under an argon atmosphere and 10% Palladium on charcoal (1 g) was added as a slurry in ethanol (30 ml). The mixture was placed under an atmosphere of hydrogen as and left to stir overnight at room temperature. TLC analysis revealed that no starting material remained. The flask was purged with argon and the catalyst was removed by filtration. The solvent was removed under reduced pressure to provide L-tert-leucine-N-2-(2-methoxyethoxy)ethylamide as a colourless oil (4.55 g, 94%). 1H--NMR; δ(CDCI3), 6.95 (1H, br s), 3.60-3.40 (8H, m), 3.34 (3H, s), 3.01 (1H, s), 1.61 (2H, br s) and 0.95 (9H, s).

Workup

  1. waitleft
  2. customThe flask was purged with argon
  3. customthe catalyst was removed by filtration
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-acefbb6d37034ac79d121c73e40cd85f
Source dataset
uspto-grants-1999_02
Patent number
US05866717

Reaction notes

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