Ethyl Acetate → HCID 67103574, compound

HRID 2080743Notes

Reaction equation

HRID 2080743 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])=[O:11])=[CH:5][CH:4]=1)#[N:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:30](OCC)(=O)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1COCC1>[NH2:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])=[O:11])=[C:7]([CH3:30])[CH:8]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 23155435HCID 23155435, compound

Product 1

HCID 67103574HCID 67103574, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound (466.4 mg) obtained in Example 12-1 was dissolved in anhydrous THF (14 ml) and the whole was cooled with ice. Lithium aluminum hydride (223.1 mg) was added thereto and the whole was stirred at room temperature for 2.5 hours. After the reaction has been stopped by addition of ethyl acetate, an aqueous potassium sodium tartrate solution was added thereto and the whole was stirred, followed by extraction with chloroform. The extract was washed with a saturated saline solution and dried with magnesium sulfate. The solvent was distilled off and the residue was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (195 mg) as a yellow oily substance.

Workup

  1. temperaturethe whole was cooled with ice
  2. stirringthe whole was stirred
  3. extractionfollowed by extraction with chloroform
  4. washThe extract was washed with a saturated saline solution
  5. dry with materialdried with magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-76741882633a46829c63dc2a8588d2b9
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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