Hydrochloric Acid → HCID 58292741, compound

HRID 1798276Notes

Reaction equation

HRID 1798276 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[N:19]=[N:20][C:21]([CH2:24][NH2:25])=[CH:22][CH:23]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)C.[Li+].[OH-].Cl>C1COCC1.O.O>[NH2:25][CH2:24][C:21]1[N:20]=[N:19][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)=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292842HCID 58292842, compound

Product 1

HCID 58292741HCID 58292741, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of [6-(6-aminomethyl-pyridazin-3-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.28 g, 0.78 mmol) in THF:H2O (1:1, 6 mL) at 0° C. was added a solution of LiOH (0.056 g, 2.35 mmol) in water (1 mL). The solution was allowed to warm to room temperature over 3 hours then acidified to pH 2 with 1N HCl at 0° C. and concentrated in vacuo. The residue was purified by preparative HPLC to give [6-(6-aminomethyl-pyridazin-3-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid (0.1 g, 38%). 1H NMR (400 MHz, DMSO): δ 8.78 (brs, 2H), 7.93 (d, J=9.2 Hz, 1H), 7.53 (d, J=9.2 Hz, 1H), 7.34 (s, 1H), 7.09 (s, 1H), 5.51 (d, J=8.8 Hz, 1H), 4.27 (d, J=5.2 Hz, 2H), 3.06 (d, J=14.8 Hz, 1H), 2.28 (s, 3H), 2.16-2.10 (m, 1H). MS (ESI) m/z=330 [M+H]+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-f9db535289bd42c7834952fd4b13515d
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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