Hydrochloric Acid → HCID 58292853, compound

HRID 1798167Notes

Reaction equation

HRID 1798167 reaction equation
C([O:3][C:4](=[O:25])[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]=[C:22]([NH2:24])[CH:21]=[CH:20][N:19]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)C.CO.O.[OH-].[Li+].Cl>C1COCC1.O>[NH2:24][C:22]1[CH:21]=[CH: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:25])=[O:3])[O:10][B:9]([OH:11])[C:8]=3[CH:12]=2)[CH:23]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 58292591HCID 58292591, compound

Product 1

HCID 58292853HCID 58292853, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [6-(4-amino-pyridin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.13 g, 0.37 mmol in THF (5 mL) and methanol (2 mL) was added lithium hydroxide monohydrate (62 mg, 1.48 mmol) in water (2 mL) at 0° C. The temperature was allowed to warm up to room temperature. The reaction mixture was stirred at room temperature for 4 h. The pH was adjusted to 3 with aqueous HCl (6 N). Prep-HPLC purification (C18 column) gave the title compound (66 mg, 55%) as a white solid. 1H NMR (300 MHz, CD3OD) δ 7.68 (1H, d), 7.16 (1H, d), 7.05 (1H, d), 6.44 (1H, dd), 5.88 (1H, s), 5.62 (1H, dd), 3.14 (1H, dd), 2.36 (3H, s), 2.30 (1H, m). MS found (electrospray): (M+H)+=315.1.

Workup

  1. customPrep-HPLC purification (C18 column)

Sources & evidence

ORD record
ord-b84bea8c748c4e50b1cd76ca5ef25996
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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