HCID 76155194, compound → HCID 76155192, compound

HRID 885703Notes

Reaction equation

HRID 885703 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH:16]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][C:29]([NH:31][OH:32])=[O:30])=[CH:22][CH:21]=2)=[O:18])=[N:13][CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[C:36]([O:35][C:34](=[O:40])[NH:33][CH:16]([CH2:15][C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][N:13]=1)[C:17]([NH:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:26][CH2:27][CH2:28][C:29]([NH:31][OH:32])=[O:30])=[CH:24][CH:25]=1)=[O:18])([CH3:39])([CH3:37])[CH3:38]

Participants

4

Reactant 1

HCID 76155194HCID 76155194, compound

Product 1

HCID 76155192HCID 76155192, compoundYield 103.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of tert-butyl 3-(5-(benzyloxy)pyridin-2-yl)-1-(4-(4-(hydroxyamino)-4-oxobutyl)phenylamino)-1-oxopropan-2-ylcarbamate (0.1 g, 0.19 mmol) and 10 mg of 10% Pd/C in 2 mL of methanol was vigorously stirred under H2 for 4 h at room temperature (monitored by TLC). It was filtered through Celite. The solvent was evaporated. The residue was purified by chromatography to give Compound 4 (0.09 g, 89%). Mp: 166-167° C.; NMR (400 MHz in CDCl3, Bruker AVANCE-400): δ 1.31 (s, 9H, Boc), 1.75 (m, 2H, CH2), 1.93 (t, 1H, CH2, J=7.10 Hz), 2.52 (t, 2H, CH2, J=7.10 Hz), 2.94 (m, 2H, CH2), 4.41 (m, 1H, CH), 6.94 (d, 1H, Ar—H, J=7.99 Hz), 7.05 (m, 1H, Ar—H), 7.08 (d, 2H, Ar—H, J=7.88 Hz), 7.21 (m, 1H, Ar—H), 7.46 (d, 2H, Ar—H, J=8.15 Hz), 8.03 (br, 1H, NH), 9.88 (br, 1H, NH), 10.32 (br, 1H, OH).

Workup

  1. filtrationIt was filtered through Celite
  2. customThe solvent was evaporated
  3. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-ccff17b934d74c819ca7e9f9d9149210
Source dataset
uspto-grants-2012_08
Patent number
US08242282B2

Reaction notes

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