Lithium Hydroxide → HCID 58292552, compound

HRID 1798231Notes

Reaction equation

HRID 1798231 reaction equation
C([O:3][C:4](=[O:26])[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][C:21]([CH2:24][NH2:25])=[CH:20][N:19]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)C.[Li+].[OH-]>C1COCC1.O>[NH2:25][CH2:24][C:21]1[N:22]=[CH:23][C:18]([O:17][C:13]2[CH:14]=[C:15]([CH3:16])[C:7]3[CH:6]([CH2:5][C:4]([OH:26])=[O:3])[O:10][B:9]([OH:11])[C:8]=3[CH:12]=2)=[N:19][CH:20]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58292664HCID 58292664, compound

Product 1

HCID 58292552HCID 58292552, compoundYield 33.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of [6-(5-aminomethyl-pyrazin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (700 mg, 2.24 mmol) in THF (16 mL) was treated with LiOH (470 mg, 11.2 mmol) in water (8 mL) at room temperature for 2 h. The reaction was concentrated to dryness. The residue was diluted with water and adjusted to pH 3. The mixture was purified by preparative HPLC to give the title compound (250 mg). 1H NMR (300 MHz, CD3OD) δ 8.48 (s, 1H), 8.35 (s, 1H), 8.21 (s, 1H), 7.18 (s, 1H), 7.07 (s, 1H), 5.70-5.63 (m, 1H), 4.29 (s, 2H), 3.18-3.12 (m, 1H), 2.40 (s, 3H), 2.36-2.28 (m, 1H). MS found: (M+H)+=330.1.

Workup

  1. concentrationThe reaction was concentrated to dryness
  2. additionThe residue was diluted with water
  3. customThe mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-7957550a480d41f4ab1ed21b6672c4ce
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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