HCID 131733796, compound → HCID 118379705, compound

HRID 708463Notes

Reaction equation

HRID 708463 reaction equation
C(OC([NH:11][C@@H:12]1[C:15](=[O:16])[NH:14][C@@H:13]1[CH2:17][N:18]1[CH:22]=[CH:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:19]1=[O:30])=O)C1C=CC=CC=1>[Pd]>[NH2:11][C@@H:12]1[C:15](=[O:16])[NH:14][C@@H:13]1[CH2:17][N:18]1[CH:22]=[CH:21][N:20]([C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])[C:19]1=[O:30]

Participants

3

Reactant 1

HCID 131733796HCID 131733796, compound

Product 1

HCID 118379705HCID 118379705, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of tert-Butyl 3-(((2R,3S)-3-(((benzyloxy)carbonyl)amino)-4-oxoazetidin-2-yl)methyl)-2-oxo-2,3-dihydro-1H-imidazole-1-carboxylate (490 mg, 1.18 mmol) and Palladium on carbon (10% wt, 140 mg) in MeOH (60 mL) was evacuated and backfilled with H2 (3×), bringing the final pressure up to 30 psi. After 2 h of stirring, the mixture was filtered through celite and concentrated in vacuo. The crude residue was purified via silica gel chromatography (MeOH-DCM, 6%), affording the title compound (50 mg, 25%).

Workup

  1. custom140 mg) in MeOH (60 mL) was evacuated
  2. filtrationthe mixture was filtered through celite and
  3. concentrationconcentrated in vacuo
  4. customThe crude residue was purified via silica gel chromatography (MeOH-DCM, 6%)

Sources & evidence

ORD record
ord-8442c1b11c844cc9b9e6c15af23b03aa
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

Loading…