Water → HCID 19348200, compound

HRID 1637281Notes

Reaction equation

HRID 1637281 reaction equation
[NH2:1][CH:2]1[C:12]2[C:13]3[C:5](=[C:6]([C:15]4[CH:20]=[CH:19][C:18]([C:21](OC)=[O:22])=[CH:17][CH:16]=4)[NH:7][C:8]=3[C:9]([Cl:14])=[CH:10][CH:11]=2)[CH2:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.CCOCC>O1CCCC1.C(OCC)(=O)C>[NH2:1][CH:2]1[C:12]2[C:13]3[C:5](=[C:6]([C:15]4[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][CH:16]=4)[NH:7][C:8]=3[C:9]([Cl:14])=[CH:10][CH:11]=2)[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 962Water2×HCID 3283Diethyl EtherHCID 19348292HCID 19348292, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19348200HCID 19348200, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A portion (170 mg) of the compound obtained in Example 171 was dissolved in anhydrous tetrahydrofuran (10 ml) and to the solution was added lithium aluminum hydride (76 mg). The mixture was stirred for 1 hour at room temperature. To the reaction mixture were added water-containing ether, then water and ethyl acetate, under cooling with ice. The insoluble matter was filtered off, followed by phase separation of the filtrate. The aqueous layer was extracted three times with ethyl acetate. The organic layers were combined, washed with water and saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (methylene chloride/methanol=2:1) to yield 109 mg (70%) of the titled compound as brown crystals.

Workup

  1. filtrationThe insoluble matter was filtered off
  2. customfollowed by phase separation of the filtrate
  3. extractionThe aqueous layer was extracted three times with ethyl acetate
  4. washwashed with water and saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (methylene chloride/methanol=2:1)

Sources & evidence

ORD record
ord-da95e07d40804f479dd76ac4cbea13f2
Source dataset
uspto-grants-2000_03
Patent number
US06040331

Reaction notes

Loading…