Lithium Hydroxide → HCID 178443426, compound

HRID 981838Notes

Reaction equation

HRID 981838 reaction equation
[CH2:1]([O:11][C:12]1[CH:30]=[CH:29][C:15]([C:16]([C:18]2[CH:19]=[C:20]([CH:26]=[CH:27][CH:28]=2)[C:21]([O:23]CC)=[O:22])=[O:17])=[CH:14][C:13]=1[CH2:31][C:32]1[NH:36][N:35]=[N:34][N:33]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[OH-].[Li+]>CC(C)=O.O>[CH2:1]([O:11][C:12]1[CH:30]=[CH:29][C:15]([C:16]([C:18]2[CH:19]=[C:20]([CH:26]=[CH:27][CH:28]=2)[C:21]([OH:23])=[O:22])=[O:17])=[CH:14][C:13]=1[CH2:31][C:32]1[NH:36][N:35]=[N:34][N:33]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 178443427HCID 178443427, compound

Product 1

HCID 178443426HCID 178443426, compoundYield 8.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A mixture of 580 mg of the product from Example 2 and 280 mg of lithium hydroxide in 10 ml of acetone and 1 ml of water were stirred for 6 hours. The mixture was concentrated in vacuo and the resulting residue was partitioned between diethyl ether and water. The layers were separated and the aqueous layer was extracted with diethyl ether. The aqueous layer was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The ethyl acetate extract was dried over magnesium sulfate and concentrated to dryness. The residue was crystallized from hexane/ethyl acetate to provide 47 mg of the title product, m.p. 147-150° C.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe resulting residue was partitioned between diethyl ether and water
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with diethyl ether
  5. extractionextracted with ethyl acetate
  6. extractionThe ethyl acetate extract
  7. dry with materialwas dried over magnesium sulfate
  8. concentrationconcentrated to dryness
  9. customThe residue was crystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-56aa5ac37742403aaf937b0499cb3302
Source dataset
uspto-grants-1991_02
Patent number
US04992576

Reaction notes

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