Ethyl Acetate → HCID 10016300, compound

HRID 1061648Notes

Reaction equation

HRID 1061648 reaction equation
S([O-])(O)=O.[Na+].[C:6]([O:10][C:11]([NH:13][C@@H:14]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:15]=[O:16])=[O:12])([CH3:9])([CH3:8])[CH3:7].C(OCC)(=O)C.[C-:30]#[N:31].[K+]>O>[C:6]([O:10][C:11]([NH:13][C@@H:14]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH:15]([OH:16])[C:30]#[N:31])=[O:12])([CH3:9])([CH3:7])[CH3:8]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 9032Potassium CyanideHCID 6998013tert-butyl N-[(2S)-1-oxo-3-phenylpropan-2-yl]carbamateHCID 23665763Sodium Bisulfite

Product 1

HCID 10016300HCID 10016300, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

A solution of sodium hydrogensulfite (0.92 g) in water (5 ml) is added to a suspension of (2S)-2-(tert-butoxycarbonyl)amino-3-phenylpropanal (2.00 g, Reference compound No. 2-1) in water (20 ml) under ice cooling, then the temperature is raised to room temperature, and the mixture is stirred overnight. Ethyl acetate (100 ml) is added to the mixture, and the whole is stirred for one hour. Then, a solution of potassium cyanide (0.58 g) in water (5 ml) is added thereto, and the whole is further stirred for four hours. The reaction mixture is extracted with ethyl acetate, and the extract is washed with saturated brine. The extract is dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the titled reference compound (1.18 g).

Workup

  1. stirringthe whole is stirred for one hour
  2. stirringthe whole is further stirred for four hours
  3. extractionThe reaction mixture is extracted with ethyl acetate
  4. washthe extract is washed with saturated brine
  5. dry with materialThe extract is dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dc776634409e40c988087d487a8b6bb4
Source dataset
uspto-grants-2005_11
Patent number
US06960575B2

Reaction notes

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