HCID 86759087, compound → HCID 53990110, compound

HRID 1359037Notes

Reaction equation

HRID 1359037 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][N:8]([S:11]([CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)(=[O:13])=[O:12])[C@@H:7]([C:25](=[O:35])[NH:26][O:27]CC2C=CC=CC=2)[CH2:6]1)=[O:4].[H][H]>CO.[Pd]>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][N:8]([S:11]([CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)(=[O:13])=[O:12])[C@@H:7]([C:25](=[O:35])[NH:26][OH:27])[CH2:6]1)=[O:4]

Participants

5

Reactant 2

HCID 86759087HCID 86759087, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53990110HCID 53990110, compoundYield 98.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (2R,4R)-2-benzyloxycarbamoyl-1-[3-(4-fluorophenoxy)-propane-1-sulfonyl]-piperidine-4-carboxylic acid methyl ester (800 mg, 1.57 mmol) and 200 mg of 5% palladium on barium sulfate in 15 mL of methanol was shaken in a Parr apparatus under a 40 psi hydrogen gas atmosphere for 2 hours. The catalyst was removed by passage of the mixture through a 0.45 μm nylon filter and the filtrate was concentrated to give 650 mg of (2R,4R)-1-[3-(4-fluorophenoxy)-propane-1-sulfonyl]-2-hydroxycarbamoyl-piperidine-4-carboxylic acid methyl ester as a white foam: MS (atmospheric pressure chemical ionization) acidic mode, 417 (M−1); 1H NMR (400 MHz, CDCl3) δ 6.94-6.97 (m, 2 H), 6.80-6.83 (m, 2 H), 4.56 (s, 1 H), 4.03 (t, 2 H, J=5.3 Hz), 3.83 (d, 1 H, J=12.9 Hz), 3.68 (s, 3 H), 3.15-3.28 (m, 3 H), 2.76 (t, 1 H, J=11.5 Hz), 2.54 (d, 1 H, J=13.5 Hz), 2.26 (d, 2 H, J=5.9 Hz), 2.02 (m, 1 H, J=13.0 Hz), 1.73-1.78 (m, 1 H), 1.56-1.62 (m, 1 H).

Workup

  1. customThe catalyst was removed by passage of the mixture through a 0.45 μm nylon
  2. filtrationfilter
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-60597cd1232d427fa415cd229a6d232a
Source dataset
uspto-grants-2003_07
Patent number
US06599890B1

Reaction notes

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