Lithium Hydroxide → [6-(5-Carbamoyl-pyrazin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid

HRID 1798239Notes

Reaction equation

HRID 1798239 reaction equation
C([O:3][C:4](=[O:27])[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]([C:24](=[O:26])[NH2:25])=[CH:20][N:19]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)C.[Li+].[OH-]>C1COCC1.O>[C: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:27])=[O:3])[O:10][B:9]([OH:11])[C:8]=3[CH:12]=2)=[N:19][CH:20]=1)(=[O:26])[NH2:25]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58292848[6-(5-Carbamoyl-pyrazin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester

Product 1

HCID 58292723[6-(5-Carbamoyl-pyrazin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acidYield 52.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of [6-(5-carbamoyl-pyrazin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (77 mg, 0.21 mmol) in THF (4 mL) was treated with LiOH (35 mg, 0.84 mmol) in water (4 mL) at room temperature for 1 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 (38 mg). 1H NMR (300 MHz, CD3OD) δ 8.76 (s, 1H), 8.46 (s, 1H), 7.29 (s, 1H), 7.16 (s, 1H), 5.73-5.69 (m, 1H), 3.33-3.18 (m, 1H), 2.42 (s, 3H), 2.38-2.33 (m, 1H). MS found: (M+H)+: 344.1.

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-35336613fa264b618be275b3df52b82e
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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