HCID 21305265, compound → HCID 21305228, compound

HRID 2084533Notes

Reaction equation

HRID 2084533 reaction equation
[CH3:1][C:2]([CH3:33])([CH3:32])[C@H:3]([NH:12][C:13](=[O:31])[C@@H:14]([CH2:19][N:20]([O:23]CC1C=CC=CC=1)[CH:21]=[O:22])[CH2:15][CH2:16][CH2:17][CH3:18])[C:4]([C:6]1[N:7]([CH3:11])[CH:8]=[CH:9][N:10]=1)=[O:5]>CO.C(OCC)(=O)C.[Pd]>[CH3:32][C:2]([CH3:1])([CH3:33])[C@H:3]([NH:12][C:13](=[O:31])[C@@H:14]([CH2:19][N:20]([CH:21]=[O:22])[OH:23])[CH2:15][CH2:16][CH2:17][CH3:18])[C:4]([C:6]1[N:7]([CH3:11])[CH:8]=[CH:9][N:10]=1)=[O:5]

Participants

5

Reactant 1

HCID 21305265HCID 21305265, compound

Product 1

HCID 21305228HCID 21305228, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2(R)-[(N-benzyloxy-N-formylamino)-methyl]-hexanoic acid-[2,2-dimethyl-1(S)-(1-methyl-1H-imidazole-2-carbonyl)-propyl]-amide. (76 mg, 0.17 mmol) in methanol (2 mL) was added a slurry of 10% Pd/C (10 mg) in ethyl acetate (1 mL). Hydrogen gas was bubbled through the reaction for 15 minutes after which time the reaction was allowed to stir under one atmosphere of hydrogen for 2 hours. The reaction was flushed with argon and filtered through glass wool. The solvents were removed in vacuo to afford the title compound as a hygroscopic white crystalline solid (43 mg, 70%).

Workup

  1. customHydrogen gas was bubbled through the reaction for 15 minutes after which time the reaction
  2. customThe reaction was flushed with argon
  3. filtrationfiltered through glass wool
  4. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-f8453030c9f04ea2af31a16e50a838ab
Source dataset
uspto-grants-2004_04
Patent number
US06716878B1

Reaction notes

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