HCID 58292807, compound → HCID 58292578, compound

HRID 1798266Notes

Reaction equation

HRID 1798266 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:24][C:25]3[CH:30]=[N:29][CH:28]=[CH:27][N:26]=3)[CH:14]=[C:15]([O:16]CC3C=CC=CC=3)[C:7]1=2)[CH3:2]>C1COCC1.CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:31])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:24][C:25]3[CH:30]=[N:29][CH:28]=[CH:27][N:26]=3)[CH:14]=[C:15]([OH:16])[C:7]1=2)[CH3:2]

Participants

4

Reactant 1

HCID 58292807HCID 58292807, compound

Product 1

HCID 58292578HCID 58292578, compoundYield 62.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A solution of [4-benzyloxy-1-hydroxy-6-(pyrazin-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (410 mg, 0.976 mmol) in THF/EtOH (20 mL, 1:1) was degassed 3 times and Pd/C (40 mg) was added. The suspension was degassed 3 times and charged with H2 at room temperature overnight. The reaction was filtered through a pad of Celite and the filtrate was concentrated to dryness. The residue was purified by preparative HPLC to give the title compound (200 mg, 62%). MS calcd for (C15H15BN2O6+H)+: 331.1. MS found: (M+H)+=331.1.

Workup

  1. additionwas added
  2. customThe suspension was degassed 3 times
  3. additioncharged with H2 at room temperature overnight
  4. filtrationThe reaction was filtered through a pad of Celite
  5. concentrationthe filtrate was concentrated to dryness
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-43817940a6d2432f951034a5d78e7c69
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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