Lithium Hydroxide → HCID 16748789, compound

HRID 2415751Notes

Reaction equation

HRID 2415751 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:16]2[O:20][N:19]=[C:18]([C:21]3[CH:22]=[C:23]([CH:29]=[CH:30][N:31]=3)[C:24]([O:26]CC)=[O:25])[N:17]=2)[CH2:11][C:12]([NH:14][OH:15])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Li+]>CO.O>[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:16]2[O:20][N:19]=[C:18]([C:21]3[CH:22]=[C:23]([CH:29]=[CH:30][N:31]=3)[C:24]([OH:26])=[O:25])[N:17]=2)[CH2:11][C:12]([NH:14][OH:15])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59059302HCID 59059302, compound

Product 1

HCID 16748789HCID 16748789, compoundYield 9.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of the title compound of Example 24 (0.44 g, 1.0 mmol) in methanol (20 mL) was added a solution of lithium hydroxide (0.09 g, 2.0 mmol) in water (7 mL) and the reaction was stirred at room temperature for 2 hours. The solvent was removed in vacuo, and the residue was diluted with water (20 mL) and dichloromethane (20 mL). The layers were separated, the organic layer was discarded and the aqueous layer was acidified to pH 4 with 2M aqueous hydrochloric acid and then extracted with dichloromethane (2×20 mL). The combined organic layers were dried (MgSO4) and the solvent was removed in vacuo to give the title compound as a white solid (0.04 g).

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue was diluted with water (20 mL) and dichloromethane (20 mL)
  3. customThe layers were separated
  4. extractionextracted with dichloromethane (2×20 mL)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-40cb46bd014547ac841b8baed27cd0af
Source dataset
uspto-grants-2004_11
Patent number
US06821972B2

Reaction notes

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