Sodium Bicarbonate → HCID 86651667, compound

HRID 337575Notes

Reaction equation

HRID 337575 reaction equation
[CH:1]1([N:4]([CH2:12][C:13]2[CH:14]=[C:15]([CH2:23][OH:24])[CH:16]=[C:17]3[C:22]=2[N:21]=[CH:20][CH:19]=[CH:18]3)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH2:3][CH2:2]1.C(=O)(O)[O-].[Na+]>ClCCl>[CH:1]1([N:4]([CH2:12][C:13]2[CH:14]=[C:15]([CH:23]=[O:24])[CH:16]=[C:17]3[C:22]=2[N:21]=[CH:20][CH:19]=[CH:18]3)[C:5](=[O:11])[O:6][C:7]([CH3:9])([CH3:10])[CH3:8])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 67061919HCID 67061919, compound

Product 1

HCID 86651667HCID 86651667, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1,1-dimethylethyl cyclopropyl{[6-(hydroxymethyl)-8-quinolinyl]methyl}carbamate (1 eq.) from the previous step and sodium bicarbonate (1.1 eq.) in dichloromethane (0.1 M) was added DMP (1.1 eq.) at 0° C. The resulting mixture was stirred at RT for 2 h before it was quenched with sat. aq. NaHSO3 and then extracted with Et2O. The combined organic extracts were washed further with 1 N aq. NaOH, water and brine, dried over Na2SO4, and filtered. Concentration of the filtrate in vacuo afforded the crude title compound as a white solid.

Workup

  1. additionwas added DMP (1.1 eq.) at 0° C
  2. customwas quenched with sat. aq. NaHSO3
  3. extractionextracted with Et2O
  4. washThe combined organic extracts were washed further with 1 N aq. NaOH, water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-b9c3b87832d14b039f2fdd6992ab929d
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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