Potassium Carbonate → HCID 67253296, compound

HRID 1798256Notes

Reaction equation

HRID 1798256 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:17][C:18]3[CH:23]=[N:22][CH:21]=[CH:20][N:19]=3)[CH:14]=[C:15]([OH:16])[C:7]1=2)[CH3:2].[C:25]([O:29][C:30](=[O:36])[NH:31][CH2:32][CH2:33]CBr)([CH3:28])([CH3:27])[CH3:26].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:17][C:18]3[CH:23]=[N:22][CH:21]=[CH:20][N:19]=3)[CH:14]=[C:15]([O:16][CH2:33][CH2:32][NH:31][C:30]([O:29][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:36])[C:7]1=2)[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 58292578HCID 58292578, compound

Product 1

HCID 67253296HCID 67253296, compoundYield 41.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of [1,4-dihydroxy-6-(pyrazin-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (from Step 7.9, 90 mg, 0.27 mmol) in DMF (10 mL) was treated with (3-bromo-propyl)-carbamic acid tert-butyl ester (92 mg, 0.41 mmol) and potassium carbonate (187 mg, 1.35 mmol) at 50° C. overnight. The reaction was concentrated to dryness. The residue was diluted with MeOH/H2O and the mixture was adjusted pH to 3. The solution was purified by preparative HPLC to afford the title compound as a white solid (53 mg). MS calcd for (C22H28BN3O8+H-Boc)+: 374.2. MS found: (M+H-Boc)+=374.2.

Workup

  1. concentrationThe reaction was concentrated to dryness
  2. additionThe residue was diluted with MeOH/H2O
  3. customThe solution was purified by preparative HPLC

Sources & evidence

ORD record
ord-9143b902791a4bf6b713ce97e5f624eb
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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