Lithium Hydroxide → HCID 19034100, compound

HRID 265876Notes

Reaction equation

HRID 265876 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][C:17]2[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[CH:19][N:18]=2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Li+].[OH-]>C1COCC1>[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][C:17]2[CH:26]=[CH:25][C:20]([C:21]([OH:23])=[O:22])=[CH:19][N:18]=2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 19034114HCID 19034114, compound

Product 1

HCID 19034100HCID 19034100, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 14-2 (650 mg, 1.2 mmol), 1N LiOH (3 mL), and THF (5 mL) was stirred at ambient temperature for 20 h. The reaction mixture was then washed with EtOAc followed by acidification with 5% KHSO4, then extraction with EtOAc. The EtOAc extract was washed with brine, dried (MgSO4) and concentrated to give 14-3 (260 mg) as a white solid. Rf 0.64 (silica, 10:2:2 (CH2Cl2 /CH3OH/AcOH).

Workup

  1. washThe reaction mixture was then washed with EtOAc
  2. extractionextraction with EtOAc
  3. extractionThe EtOAc extract
  4. washwas washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-68955fefbfe648ca965cb1f87433378c
Source dataset
uspto-grants-1997_07
Patent number
US05648368

Reaction notes

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