Hydrochloric Acid → HCID 58292851, compound

HRID 1798269Notes

Reaction equation

HRID 1798269 reaction equation
[C:1]([CH2:3][O:4][C:5]1[C:13]2[CH:12]([CH2:14][C:15]([O:17]CC)=[O:16])[O:11][B:10]([OH:20])[C:9]=2[CH:8]=[C:7]([O:21][C:22]2[CH:27]=[N:26][CH:25]=[CH:24][N:23]=2)[CH:6]=1)#N.[OH-:28].[Li+].Cl.[CH3:31][CH2:32][OH:33]>O>[CH2:32]([O:33][C:1](=[O:28])[CH2:3][O:4][C:5]1[C:13]2[CH:12]([CH2:14][C:15]([OH:17])=[O:16])[O:11][B:10]([OH:20])[C:9]=2[CH:8]=[C:7]([O:21][C:22]2[CH:27]=[N:26][CH:25]=[CH:24][N:23]=2)[CH:6]=1)[CH3:31]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 3939Lithium HydroxideHCID 58292593HCID 58292593, compound

Product 1

HCID 58292851HCID 58292851, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of ethyl 2-(4-(cyanomethoxy)-1-hydroxy-6-(pyrazin-2-yloxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (100 mg, 0.271 mmol) in EtOH (4 mL) was added an aqueous solution of lithium hydroxide (21.9 mg, 0.54 mmol) in water (1 mL). The reaction mixture was stirred at room temperature overnight and acidified with 1N HCl to pH=3. The resulting mixture was extracted with EtOAc (2×20 mL) and the combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by prep HPLC to give the title compound as a white powder (30 mg. Yield: 26%). 1H NMR (400 MHz, DMSO-d6) δ 12.34 (s, 1H), 9.31 (s, 1H), 8.55 (s, 1H), 8.40 (d, J=2.4 Hz, 1H), 8.23 (t, J=1.2 Hz, 1H), 7.06 (d, J=1.2 Hz, 1H), 7.00 (s, 1H), 5.51 (m, 1H), 4.48 (m, 2H), 4.16 (m, 2H), 3.37 (d, J=2.0 Hz, 1H), 2.21 (m, 1H), 1.16 (m, 3H). MS (ESI) m/z=389 [M+H]+.

Workup

  1. extractionThe resulting mixture was extracted with EtOAc (2×20 mL)
  2. dry with materialthe combined organic layers were dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-f2881c012c714122a3773ecb35fd82db
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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