Hydrochloric Acid → HCID 67252443, compound

HRID 1798125Notes

Reaction equation

HRID 1798125 reaction equation
[CH3:1][N:2]([CH3:23])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH3:22])[C:9]2[CH:13]([CH2:14][C:15]([O:17]CC)=[O:16])[O:12][B:11]([OH:20])[C:10]=2[CH:21]=1.[Li+].[OH-].[ClH:26]>C1COCC1.O.O>[ClH:26].[CH3:23][N:2]([CH3:1])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH3:22])[C:9]2[CH:13]([CH2:14][C:15]([OH:17])=[O:16])[O:12][B:11]([OH:20])[C:10]=2[CH:21]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292774HCID 58292774, compound

Product 1

HCID 67252443HCID 67252443, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of ethyl 2-(6-(2-(dimethylamino)ethoxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (crude) in 15 ml of THF/H2O (2/1) was added LiOH (42 mg, 1.0 mmol) in 5 ml H2O at 0° C. The reaction mixture was stirred at room temperature for 1.5 h and acidified by 1.0 N HCl to pH=6. The resulting mixture was extracted with EtOAc (3×20 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 solid (35 mg, yield: 15%, two steps). 1H NMR (400 MHz, DMSO-d) δ9.15 (s, 1H), 7.08 (d, J=1.6 Hz, 1H), 6.89 (d, J=1.6 Hz, 1H), 5.46-5.43 (m, 1H), 4.24-4.22 (m, 2H), 4.09 (m, 1H), 3.24 (m, 2H), 3.16 (s, 3H), 3.05-3.01 (m, 1H), 2.65 (s, 6H), 2.26 (s, 3H), 2.09-2.02 (m, 1H); MS (ESI) m/z=294 [M+H]+.

Workup

  1. extractionThe resulting mixture was extracted with EtOAc (3×20 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-901a3292288a4dbcbdb2dbb59d668802
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

Loading…