Lithium hydroxide, monohydrate → HCID 15896092, compound

HRID 347652Notes

Reaction equation

HRID 347652 reaction equation
C([O:3][C:4](=[O:31])[CH2:5][NH:6][C:7]([NH:9][CH2:10][C:11]1[CH:29]=[CH:28][C:14]([C:15]([N:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:16])=[CH:13][C:12]=1[CH3:30])=[O:8])C.O.[OH-].[Li+]>C1COCC1.O>[C:4]([CH2:5][NH:6][C:7]([NH:9][CH2:10][C:11]1[CH:29]=[CH:28][C:14]([C:15]([N:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:16])=[CH:13][C:12]=1[CH3:30])=[O:8])([OH:31])=[O:3]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 15896091HCID 15896091, compound

Product 1

HCID 15896092HCID 15896092, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the ethyl ester from Example 32 (0.050 g, 0.10 mmol) in THF (20 ml) and water (5 ml) was added lithium hydroxide monohydrate (0.020 g, 0.45 mmol). The mixture was stirred at room temperature for 4 h. The mixture was concentrated in vaicuo and the residue diluted with water then washed with diethyl ether. The aqueous layer was acidified to pH 1 by addition of 1M HCl and extracted with EtOAc (3 times). The combined organic extracts were washed with brine, dried over Na2SO4, and concentrated in vacuo to give a white solid; yield 0.046 g (99%).

Workup

  1. concentrationThe mixture was concentrated in vaicuo
  2. additionthe residue diluted with water
  3. washthen washed with diethyl ether
  4. additionThe aqueous layer was acidified to pH 1 by addition of 1M HCl
  5. extractionextracted with EtOAc (3 times)
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customto give a white solid

Sources & evidence

ORD record
ord-0c7a7dd606994675ad3791da0ceb85d6
Source dataset
uspto-grants-2007_02
Patent number
US07176195B2

Reaction notes

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