HCID 87232360, compound → HCID 123919966, compound

HRID 885707Notes

Reaction equation

HRID 885707 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH:16]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[C:17]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27](=[O:30])[NH:28][OH:29])=[CH:23][CH:22]=2)=[O:18])=[N:13][CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[C:34]([O:33][C:32](=[O:38])[NH:31][CH:16]([CH2:15][C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][N:13]=1)[C:17]([NH:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27](=[O:30])[NH:28][OH:29])=[CH:23][CH:22]=1)=[O:18])([CH3:37])([CH3:35])[CH3:36]

Participants

4

Reactant 1

HCID 87232360HCID 87232360, compound2×

Product 1

HCID 123919966HCID 123919966, compoundYield 74.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of t-butyl 3-(5-(benzyloxy)pyridin-2-yl)-1-(4-(hydroxyl-carbamoyl)benzylamino)-1-oxopropan-2-ylcarbamate (Compound 7) (0.26 g, 0.5 mmol) and 26 mg of 10% Pd/C in 2 mL of methanol was vigorously stirred under H2 for 4 h at room temperature and then filtered through Celite. The solvent was evaporated. The residue was purified by chromatography to give oily Compound 9 (0.16 g, 73%). NMR (400 MHz in CDCl3, Bruker AVANCE-400) : 1.28 (s, 9H, Boc), 3.15 (m, 2H, CH2), 4.28 (t, 2H, CH2, J=5.12 Hz), 4.36 (m, 1H, CH), 7.05-7.25 (m, 4H, Ar—H), 7.64-7.84 (m, 3H, Ar—H), 8.23 (br, 1H, NH), 8.51 (br, 1H, NH), 10.18 (br, 1H, NH), 11.16 (br, 1H, OH).

Workup

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

Sources & evidence

ORD record
ord-4308c67b2ca240599bc06775676437ea
Source dataset
uspto-grants-2012_08
Patent number
US08242282B2

Reaction notes

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