HCID 25242117, compound → HCID 25241948, compound

HRID 2219024Notes

Reaction equation

HRID 2219024 reaction equation
C([O:8][CH2:9][CH2:10][N:11]1[CH2:17][C@H:16]([NH:18][C:19](=[O:34])[C:20]([OH:33])([CH3:32])[C:21]([NH:23][CH2:24][C:25]([F:31])([F:30])[C:26]([F:29])([F:28])[F:27])=[O:22])[C:15](=[O:35])[NH:14][C:13]2[CH:36]=[CH:37][CH:38]=[CH:39][C:12]1=2)C1C=CC=CC=1>CO.[Pd]>[OH:33][C:20]([CH3:32])([C:21]([NH:23][CH2:24][C:25]([F:30])([F:31])[C:26]([F:27])([F:28])[F:29])=[O:22])[C:19]([NH:18][C@H:16]1[CH2:17][N:11]([CH2:10][CH2:9][OH:8])[C:12]2[CH:39]=[CH:38][CH:37]=[CH:36][C:13]=2[NH:14][C:15]1=[O:35])=[O:34]

Participants

4

Reactant 1

HCID 25242117HCID 25242117, compound

Product 1

HCID 25241948HCID 25241948, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 26 mg of N-[(S)-1-(2-benzyloxy-ethyl)-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl]-2-hydroxy-2-methyl-N′-(2,2,3,3,3-pentafluoro-propyl)-malonamide in 2.0 ml of methanol was treated with 10 mg of palladium on carbon (10%) and stirred for 3 days under an atmosphere of hydrogen. During this period of time, the catalyst was replaced three times after filtration of the reaction mixture over Dicalit. For the final working-up, the reaction mixture was filtrated over Dicalit and the solvent evaporated under reduced pressure. After separation of mainly unchanged starting material by chromatography on silica gel using a gradient of heptane/ethyl acetate=100/0 to 20/80 as the eluent, 6 mg (29% of theory) of the title compound were obtained as a white foam; MS (m/e): 469 (M+H)+.

Workup

  1. waitDuring this period of time
  2. filtrationafter filtration of the reaction mixture over Dicalit
  3. filtrationFor the final working-up, the reaction mixture was filtrated over Dicalit
  4. customthe solvent evaporated under reduced pressure
  5. customAfter separation
  6. customwere obtained as a white foam

Sources & evidence

ORD record
ord-71c601917abf43bdb07d45fcb8344153
Source dataset
uspto-grants-2008_08
Patent number
US07414049B2

Reaction notes

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