Ethyl Acetate → HCID 86723551, compound

HRID 1913535Notes

Reaction equation

HRID 1913535 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][C:12]([N:14]([CH2:22][CH:23]([CH2:29][CH3:30])[C:24](OCC)=[O:25])C(OC(C)(C)C)=O)=[O:13])([CH3:10])([CH3:9])[CH3:8].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].C(OCC)(=O)C>O1CCCC1>[C:7]([O:11][C:12](=[O:13])[NH:14][CH2:22][CH:23]([CH2:24][OH:25])[CH2:29][CH3:30])([CH3:8])([CH3:9])[CH3:10]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 86675832HCID 86675832, compound

Product 1

HCID 86723551HCID 86723551, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (153 mg) was suspended in tetrahydrofuran (20 mL). To the suspension, a solution of the compound obtained in Step 4 in tetrahydrofuran (2 mL) was added dropwise under ice cooling, and the mixture was then stirred overnight. To the reaction solution, sodium sulfate decahydrate was added under ice cooling. Subsequently, ethyl acetate was added thereto, and the mixture was stirred. After celite filtration, the solvent in the filtrate was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate=9/1-3/7) to obtain the title compound (168 mg).

Workup

  1. stirringthe mixture was stirred
  2. filtrationAfter celite filtration
  3. distillationthe solvent in the filtrate was distilled off under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate=9/1-3/7)

Sources & evidence

ORD record
ord-f1c1f84e47c948519e4fd4c3fb00f175
Source dataset
uspto-grants-2013_12
Patent number
US08609710B2

Reaction notes

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