Hydrochloric Acid → HCID 46884278, compound

HRID 1483665Notes

Reaction equation

HRID 1483665 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[CH:8][C:9]([O:11][C:12]3[CH:22]=[CH:21][C:15]([C:16]([O:18]CC)=[O:17])=[CH:14][N:13]=3)=[CH:10][C:5]=2[CH2:4][O:3]1.Cl>C1COCC1.[OH-].[Na+]>[OH:1][B:2]1[C:6]2[CH:7]=[CH:8][C:9]([O:11][C:12]3[CH:22]=[CH:21][C:15]([C:16]([OH:18])=[O:17])=[CH:14][N:13]=3)=[CH:10][C:5]=2[CH2:4][O:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 46830302HCID 46830302, compound

Product 1

HCID 46884278HCID 46884278, compoundYield 94.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

The title bis-acid compound was prepared by hydrolysis of the corresponding carboxylic acid ethyl ester. Ethyl 6-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yloxy)nicotinate (2.99 g, 10 mmol) was dissolved in freshly opened THF (100 mL), and 1N NaOH (38 mL) was added. The mixture was stirred at room temperature under N2 overnight. Then 6N HCl (6.5 mL) was added, rotary evaporated to remove THF, filtered and washed with water and then hexane. The solid was dried overnight under high vacuum to afford the title bis-acid compound (2.57 g, 9.48 mmol, yield 94.8%) as a slightly brown solid.

Workup

  1. additionwas added
  2. customrotary evaporated
  3. customto remove THF
  4. filtrationfiltered
  5. washwashed with water
  6. customThe solid was dried overnight under high vacuum

Sources & evidence

ORD record
ord-2f39471ae2b34b83b3149e4e1c744a78
Source dataset
uspto-grants-2016_08
Patent number
US09416146B2

Reaction notes

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