Hydrochloric Acid → HCID 58292792, compound

HRID 1798236Notes

Reaction equation

HRID 1798236 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](=[NH:26])[NH2:25])=[CH:20][N:19]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)C.O.[OH-].[Li+].Cl>C1COCC1.CO.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)(=[NH:25])[NH2:26]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 58292710HCID 58292710, compound

Product 1

HCID 58292792HCID 58292792, compoundYield 49%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

[6-(5-Carbamimidoyl-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) was dissolved in THF (3 mL) and methanol (1.2 mL). To this was added lithium hydroxide monohydrate (70 mg, 1.7 mmol) in water (1.2 mL) at 0° C. The reaction was warmed up to room temperature and stirred for 4 h. The reaction mixture was acidified to pH 3 with aqueous HCl (6 N). The solvent was removed. Prep-HPLC separation (C18 column) of the reaction mixture gave the title compound (35 mg, 49%) as a white solid. 1H NMR (300 MHz, CD3OD) δ 8.42 (1H, s), 8.20 (1H, s), 6.85 (1H, s), 6.65 (1H, s), 5.18 (1H, dd), 2.64 (1H, dd), 2.16 (3H, s), 2.15 (1H, m). MS found (electrospray): (M+H)+=343.2.

Workup

  1. customThe solvent was removed
  2. customPrep-HPLC separation (C18 column) of the reaction mixture

Sources & evidence

ORD record
ord-71b35c86d8264830964c4b85e6c2f03b
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

Loading…