Sodium Hydroxide → HCID 68645793, compound

HRID 339614Notes

Reaction equation

HRID 339614 reaction equation
C([O:3][C:4](=[O:23])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[C:14]2[B:15]([OH:22])[O:16][CH:17]([CH2:18][N+:19]([O-:21])=[O:20])[C:13]=2[CH:12]=[CH:11][CH:10]=1)C.[OH-].[Na+]>CO.O>[OH:22][B:15]1[C:14]2[C:9]([O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:23])=[O:3])=[CH:10][CH:11]=[CH:12][C:13]=2[CH:17]([CH2:18][N+:19]([O-:21])=[O:20])[O:16]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68646048HCID 68646048, compound

Product 1

HCID 68645793HCID 68645793, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A mixture of 4-(1-hydroxy-3-nitromethyl-1,3-dihydro-benzo[c][1,2]oxaborol-7-yloxy)-butyric acid ethyl ester (2.51 g, 7.78 mmol), 10% NaOH (17 mL), and 1:1 MeOH/H2O (70 mL) was stirred at rt for 5 h. The MeOH was removed in vacuo and the remaining aqueous layer was acidified to pH 1 using 2 M HCl. The aqueous layer was then extracted with EtOAc. The organic fractions were washed with brine, dried (MgSO4), and concentrated in vacuo to give the title compound as a pale yellow foam: yield 1.85 g (81%).

Workup

  1. customThe MeOH was removed in vacuo
  2. extractionThe aqueous layer was then extracted with EtOAc
  3. washThe organic fractions were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2df69d53a6244770b6ae0a464fee96de
Source dataset
uspto-grants-2014_11
Patent number
US08895534B2

Reaction notes

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