Ethyl Acetate → HCID 61154753, compound

HRID 19401Notes

Reaction equation

HRID 19401 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:13](=[O:21])[NH:14][C:15]1[CH:20]=[N:19][CH:18]=[CH:17][N:16]=1)[CH2:9][CH:10]([CH3:12])[CH3:11])(C)(C)C.FC(F)(F)C(O)=O.ClCCl.C(OCC)(=O)C>O>[N:16]1[CH:17]=[CH:18][N:19]=[CH:20][C:15]=1[NH:14][C:13](=[O:21])[C@@H:8]([NH2:7])[CH2:9][CH:10]([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21863450Trifluoroacetic acid methylene chlorideHCID 66894943[(S)-3-Methyl-1-(pyrazin-2-ylcarbamoyl)-butyl]-carbamic acid t-butyl ester

Product 1

HCID 61154753HCID 61154753, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

[(S)-3-Methyl-1-(pyrazin-2-ylcarbamoyl)-butyl]-carbamic acid t-butyl ester (0.645 g, 2.09 mmol) was treated with a 30% trifluoroacetic acid/dichloromethane (10 mL) solution at 0° C. and the resulting mixture allowed to warm to room temperature over 1.5 h. At this time the mixture was partioned between ethyl acetate and water and the layers separated. The aqueous phase was made basic (pH=10) by the addition of solid sodium hydroxide. The basic aqueous phase was extracted with ethyl acetate (3×) and the ethyl acetate layers were combined, dried over sodium sulfate, filtered and concentrated in vacuo to afford (S)-2-amino-4-methyl-pentanoic acid pyrazin-2-ylamide (0.341 g, 78%).

Workup

  1. customthe layers separated
  2. additionby the addition of solid sodium hydroxide
  3. extractionThe basic aqueous phase was extracted with ethyl acetate (3×)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2233b4189f464a808382746f06db9a78
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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