Lithium hydroxide, monohydrate → HCID 15896092, compound

HRID 432587Notes

Reaction equation

HRID 432587 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 5 (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 vacuo 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 vacuo
  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-870f3672121247cd932f677760e88eb7
Source dataset
uspto-grants-2003_12
Patent number
US06664249B1

Reaction notes

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