HCID 178418361, compound → HCID 178454254, compound

HRID 708498Notes

Reaction equation

HRID 708498 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[N:22]=[C:21]([CH2:23][NH:24][C:25](=[N:46][C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[N:26]([CH2:34][CH:35]2[CH2:38][N:37]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:36]2)[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH:20]=[N:19]1)=O)C1C=CC=CC=1.[H][H]>CCO.CO.[Pd]>[NH2:11][C@@H:12]1[C:15](=[O:16])[NH:14][C@@H:13]1[CH2:17][N:18]1[N:22]=[C:21]([CH2:23][NH:24][C:25](=[N:46][C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[N:26]([CH2:34][CH:35]2[CH2:36][N:37]([C:39]([O:41][C:42]([CH3:43])([CH3:45])[CH3:44])=[O:40])[CH2:38]2)[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH:20]=[N:19]1

Participants

6

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178454253HCID 178454253, compound

Product 1

HCID 178454254HCID 178454254, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 3-((3-((2-(((2R,3S)-3-(((benzyloxy)carbonyl)amino)-4-oxoazetidin-2-yl)methyl)-2H-1,2,3-triazol-4-yl)methyl)-1,2-bis(tert-butoxycarbonyl)guanidino)methyl)azetidine-1-carboxylate (390 mg, 0.526 mmol) in EtOH (10 mL) and MeOH (10.00 mL) was added Pd/C (5%, 112 mg, 53 μmol) and hydrogen baloon after evacuation and backfilled with H2. After 1 h, the reaction mixture was filtered over celite pad, and the filtrate was concentrated in vacuo to afford title compound (302 mg, 95%). The crude residue was used as such in the following step. LCMS: Rt=0.74 min, m/z=608.4 (M+1) Method 2m_acidic.

Workup

  1. filtrationthe reaction mixture was filtered over celite pad
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-57f128bcf0844d8592a397b1799dc9a5
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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