HCID 59718717, compound → HCID 59718684, compound

HRID 2219027Notes

Reaction equation

HRID 2219027 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])[N:14]([CH2:36][C:37]([F:40])([F:39])[F:38])[C:13]2[CH:41]=[CH:42][CH:43]=[CH:44][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:31])([F:30])[C:26]([F:27])([F:28])[F:29])=[O:22])[C:19]([NH:18][C@@H:16]1[C:15](=[O:35])[N:14]([CH2:36][C:37]([F:39])([F:40])[F:38])[C:13]2[CH:41]=[CH:42][CH:43]=[CH:44][C:12]=2[N:11]([CH2:10][CH2:9][OH:8])[CH2:17]1)=[O:34]

Participants

4

Reactant 1

HCID 59718717HCID 59718717, compound

Product 1

HCID 59718684HCID 59718684, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 72 mg of the first eluting epimer (R or S)-N-[(S)-5-(2-benzyloxy-ethyl)-2-oxo-1-(2,2,2-trifluoro-ethyl)-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 3.0 ml of methanol was treated with 24 mg of palladium on carbon (10%) and stirred for 24 hours under an atmosphere of hydrogen. For the working-up, the reaction mixture was filtrated over Dicalit and the solvent evaporated under reduced pressure. The crude material was purified by chromatography on silica gel using a gradient of heptane/ethyl acetate=100/0 to 30/60 as the eluent, and 46 mg (79% of theory) of the title compound were obtained as a white foam; MS (m/e): 551 (M+H)+.

Workup

  1. filtrationthe reaction mixture was filtrated over Dicalit
  2. customthe solvent evaporated under reduced pressure
  3. customThe crude material was purified by chromatography on silica gel using a gradient of heptane/ethyl acetate=100/0 to 30/60 as the eluent, and 46 mg (79% of theory) of the title compound
  4. customwere obtained as a white foam

Sources & evidence

ORD record
ord-484761b7ea864522b88499270d1e9bba
Source dataset
uspto-grants-2008_08
Patent number
US07414049B2

Reaction notes

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