Water → HCID 117736214, compound

HRID 1482187Notes

Reaction equation

HRID 1482187 reaction equation
FC(F)(F)C(O)=O.[O:8]=[C:9]([S:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:10][CH2:11][C@H:12]([NH:20][C:21](=[O:26])[CH2:22][CH2:23][CH:24]=[CH2:25])[C:13]([O:15][C:16](C)(C)[CH3:17])=[O:14].C([N:36](C(C)C)C(C)C)C.O>ClCCl.BrCC#N>[O:8]=[C:9]([S:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:10][CH2:11][C@H:12]([NH:20][C:21](=[O:26])[CH2:22][CH2:23][CH:24]=[CH2:25])[C:13]([O:15][CH2:16][C:17]#[N:36])=[O:14]

Participants

7

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 89668257HCID 89668257, compound

Product 1

HCID 117736214HCID 117736214, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 11534BromoacetonitrileSolvent

Procedure

Trifluoroacetic acid (3.85 ml, 51.8 mmol) was added to a solution of (S)-tert-butyl 5-oxo-2-(pent-4-enamido)-5-(phenylthio)pentanoate (Compound 1e-IIF) (978 mg, 2.59 mmol) in dichloromethane (6.74 ml), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was then concentrated under reduced pressure. N-Ethyl-N-isopropylpropan-2-amine (1.30 ml, 7.47 mmol) was added to a solution of the resulting residue in 2-bromoacetonitrile (8 ml), and the mixture was stirred at room temperature for 30 minutes. After adding water to the reaction mixture, purification by reverse phase silica gel column chromatography (10 mM aqueous ammonium acetate solution/methanol=60/40→20/80) afforded (S)-cyanomethyl 5-oxo-2-(pent-4-enamido)-5-(phenylthio)pentanoate (Compound 1g-IIF) (722 mg, 64%).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. customto the reaction mixture, purification by reverse phase silica gel column chromatography (10 mM aqueous ammonium acetate solution/methanol=60/40→20/80)

Sources & evidence

ORD record
ord-eb6e048eb63a48bba7bf47dcccab0108
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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