Water → HCID 69689115, compound

HRID 1368074Notes

Reaction equation

HRID 1368074 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH:21]1[CH2:23][CH2:22]1)[C:13](=[O:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O>C(O)C>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH:21]1[CH2:23][CH2:22]1)[CH:13]([OH:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 69689136HCID 69689136, compound

Product 1

HCID 69689115HCID 69689115, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-(S)-benzyloxycarbonylamino-4-cyclopropyl-3-oxobutanoate (1.526 g, 4.778 mmol) was dissolved in anhydrous ethanol (15 ml), and the solution was mixed with sodium borohydride (94.6 mg, 2.50 mmol)under ice-cooling and stirred at the same temperature for 1 hour. Under ice-cooling, the reaction solution was mixed with water (20 ml) and then ethanol was evaporated under a reduced pressure. The thus obtained residue was mixed with chloroform (50 ml) and stirred, and then the thus separated chloroform layer was washed with saturated sodium chloride aqueous solution (30 ml) and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated to dryness under a reduced pressure, thereby obtaining 1.509 g (98.3%) of the title compound as a colorless oil. This product was used in the subsequent reaction without purification.

Workup

  1. temperaturecooling
  2. temperatureUnder ice-cooling
  3. customethanol was evaporated under a reduced pressure
  4. additionThe thus obtained residue was mixed with chloroform (50 ml)
  5. stirringstirred
  6. washthe thus separated chloroform layer was washed with saturated sodium chloride aqueous solution (30 ml)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationAfter filtration
  9. customthe solvent was evaporated to dryness under a reduced pressure

Sources & evidence

ORD record
ord-146af5a00fdf42e38cdecf29f50c1783
Source dataset
uspto-grants-2003_06
Patent number
US06573260B1

Reaction notes

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