Water → HCID 19348229, compound

HRID 1637263Notes

Reaction equation

HRID 1637263 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][CH:8]1[C:18]2[C:19]3[C:11](=[C:12]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[N:13]([CH2:20][C:21](OC)=[O:22])[C:14]=3[CH:15]=[CH:16][CH:17]=2)[CH2:10][CH2:9]1.O>O1CCCC1>[NH2:7][CH:8]1[C:18]2[C:19]3[C:11](=[C:12]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:13]([CH2:20][CH2:21][OH:22])[C:14]=3[CH:15]=[CH:16][CH:17]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 962WaterHCID 19348283HCID 19348283, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19348229HCID 19348229, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (35 mg) was suspended in anhydrous tetrahydrofuran (THF; 1 ml) and to the suspension was added a solution of the compound (197 mg) obtained in Example 115 in anhydrous THF (7 ml) at room temperature. The mixture was stirred for 5 minutes. To the reaction mixture were slowly added water, then 1N aqueous solution of sodium hydroxide, followed by extraction with two portions of ethyl acetate. The organic layer was washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was crystallized from ether to yield 149 mg (83%) of the titled compound as pale yellow crystals.

Workup

  1. extraction1N aqueous solution of sodium hydroxide, followed by extraction with two portions of ethyl acetate
  2. washThe organic layer was washed with water and saturated aqueous solution of sodium chloride successively
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was crystallized from ether

Sources & evidence

ORD record
ord-b4125f71e7b84703b4f0668d1ca85a20
Source dataset
uspto-grants-2000_03
Patent number
US06040331

Reaction notes

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