Hydrochloric Acid → HCID 67252166, compound

HRID 1798233Notes

Reaction equation

HRID 1798233 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([O:11][C:12]2[CH:13]=[C:14]([CH3:28])[C:15]3[CH:19]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[O:18][B:17]([OH:26])[C:16]=3[CH:27]=2)=[CH:7][N:6]=1)=[O:4].[Li+].[OH-].Cl>C1COCC1.O>[CH2:24]([O:23][C:21]([CH2:20][CH:19]1[O:18][B:17]([OH:26])[C:16]2[CH:27]=[C:12]([O:11][C:8]3[N:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=3)[CH:13]=[C:14]([CH3:28])[C:15]1=2)=[O:22])[CH3:25]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67251860HCID 67251860, compound

Product 1

HCID 67252166HCID 67252166, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(3-ethoxycarbonylmethyl-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-6-yloxy)-pyrazine-2-carboxylic acid methyl ester (2.15 g, 11.3 mmol) in THF (42 mL) was added LiOH (0.47 g, 22.6 mmol) in water (21 mL). The mixture was stirred at room temperature for 1 h and acidified by 1N HCl to pH 3. The mixture was extracted by ethyl acetate, and the organic layer was washed with water and brine, dried from Na2SO4 and concentrated. The residue was purified by column chromatography (silica, DCM/MeOH=9:1) affording the title compound (1.9 g, 92%) as a white solid. 1H NMR (CDCl3) δ 8.96 (s, 1H), 8.42 (s, 1H), 7.31 (d, 1H), 7.03 (d, 1H), 5.68 (dd, 1H), 4.10 (q, 2H), 3.11 (dd, 1H), 2.43 (m, 1H), 2.40 (s, 3H), 1.25 (t, 3H).

Workup

  1. extractionThe mixture was extracted by ethyl acetate
  2. washthe organic layer was washed with water and brine
  3. dry with materialdried from Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (silica, DCM/MeOH=9:1)

Sources & evidence

ORD record
ord-f58c9148e1034115af243f0417a71afa
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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