Lithium Hydroxide → HCID 67215068, compound

HRID 2421622Notes

Reaction equation

HRID 2421622 reaction equation
[Li+].[OH-].C[O:4][C:5](=[O:25])[CH2:6][C:7]1[CH:8]=[C:9]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:10]=[C:11]([C:13](=[O:18])[NH:14][CH2:15][CH2:16][CH3:17])[CH:12]=1.CO.O>O>[CH2:15]([NH:14][C:13]([C:11]1[CH:12]=[C:7]([CH2:6][C:5]([OH:25])=[O:4])[CH:8]=[C:9]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:10]=1)=[O:18])[CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 22242641Methanol--water (1/1)HCID 67214559HCID 67214559, compound

Product 1

HCID 67215068HCID 67215068, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of LiOH (800 μL of a 2 M solution in H2O) was added to a solution of 68G (50 mg, 0.16 mmol) in 4 mL of a 3:1 mixture MeOH/H2O. After 1 hour, the reaction was complete as shown by TLC. The reaction mixture was then concentrated and the residue was dissolved in water and HCl 10% was then added. As no product precipitated, the aqueous solution was extracted 3 times with AcOEt. The combined organic layers were washed with brine, dried over MgSO4 and concentrated. A white foamy solid was obtained and used in the next step without further purification (47 mg, quantitative). NMR 1H (ppm, DMSO-d6): 7.86 (s, 1H), 7.61-7.60 (m, 3H), 7.57 (s, 1H), 7.46-7.33 (m, 3H), 6.16 (br, s, 1H), 3.72 (s, 2H), 3.70 (s, 3H), 3.46-3.39 (m, 2H), 1.64 (sext., J3=7.43 Hz, 2H), 0.98 (t., J3=7.50 Hz, 3H).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. dissolutionthe residue was dissolved in water
  3. additionHCl 10% was then added
  4. customAs no product precipitated
  5. extractionthe aqueous solution was extracted 3 times with AcOEt
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customA white foamy solid was obtained
  10. customused in the next step without further purification (47 mg, quantitative)

Sources & evidence

ORD record
ord-7ae895ad40c64299b88247cc2dacfd9d
Source dataset
uspto-grants-2011_06
Patent number
US07956216B2

Reaction notes

Loading…