HCID 101501226, compound → Acetyl-L-leucyl-L-leucine

HRID 861306Notes

Reaction equation

HRID 861306 reaction equation
[NH:1]([C:25]([CH3:27])=[O:26])[C@H:2]([C:7]([NH:9][C@H:10]([C:15]([O:17]CC1C=CC=CC=1)=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[H][H]>CC(=O)OCC.[OH-].[OH-].[Pd+2]>[NH:1]([C:25]([CH3:27])=[O:26])[C@H:2]([C:7]([NH:9][C@H:10]([C:15]([OH:17])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5]

Participants

5

Reactant 2

HCID 101501226HCID 101501226, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10968127Acetyl-L-leucyl-L-leucineYield 87.7%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of N-Ac-L-Leu-L-Leu-OBn (9.09 g, 23.9 mmol) in EA (100 mL) at R.T. was added 20% palladium hydroxide on carbon (Pd (OH)2 /C) (0.9 g, 10% by weight). The reaction mixture was placed under 20 psi hydrogen (H2). After 1 h the reaction mixture was filtered through celite and concentrated in vacuo to give N-Ac-L-Leu-L-Leu-OH as a white solid (6.0 g, 87.67%): 1H NMR (300 MHz, CDCl3) δ 0.82-0.90 (m, 12H), 1.39-1.82 (m, 9H), 4.18-4.34 (m, 2H), 7.94-8.13 (m, 2H) ppm.

Workup

  1. filtrationAfter 1 h the reaction mixture was filtered through celite and
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6c1d134d2b4d41ed80bf2dac641e788d
Source dataset
uspto-grants-1998_02
Patent number
US05714471

Reaction notes

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