Lithium Hydroxide → HCID 54351775, compound

HRID 2380161Notes

Reaction equation

HRID 2380161 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][CH2:5][C:6]1[O:7][C:8]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[N:23]([CH3:24])[C:22]4[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=4[N:20]=3)=[CH:13][CH:12]=2)[N:10]=1.[Li+].[OH-].ClCCl.C(O)C>O1CCCC1>[CH3:24][N:23]1[C:22]2[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=2[N:20]=[C:19]1[CH2:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[N:10]=[C:6]([CH2:5][CH2:4][C:3]([OH:35])=[O:2])[O:7][C:8]=2[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 15227899HCID 15227899, compoundHCID 21584144Dichloromethane ethanol

Product 1

HCID 54351775HCID 54351775, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the ester (1 g, 2.14 mmole) of Step A, in tetrahydrofuran (13 mL) containing 1N-LiOH (6.42 mL) is stirred under nitrogen at room temperature for 1 hour (TLC, dichloromethane-ethanol 9:1 ). The solvent is evaporated, water added and the pH adjusted to 6.5 with 10% acetic acid. The fight yellow precipitate is collected, washed with water and dried in vacuo. It is redissolved in hot ethyl acetate (containing enough methanol to obtain a clear solution), concentrated to a smaller volume and cooled in an ice bath. The crystals are collected and dried (0.642 g, 66.2%, m.p. 222°-224° C.).

Workup

  1. customThe solvent is evaporated
  2. additionwater added
  3. customThe fight yellow precipitate is collected
  4. washwashed with water
  5. customdried in vacuo
  6. dissolutionIt is redissolved in hot ethyl acetate (
  7. additioncontaining enough methanol
  8. customto obtain a clear solution),
  9. concentrationconcentrated to a smaller volume
  10. temperaturecooled in an ice bath
  11. customThe crystals are collected
  12. customdried (0.642 g, 66.2%, m.p. 222°-224° C.)

Sources & evidence

ORD record
ord-548805b3ff364e47af625e536eaacb95
Source dataset
uspto-grants-1994_11
Patent number
US05364944

Reaction notes

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