Ammonium Chloride → HCID 117735204, compound

HRID 1482179Notes

Reaction equation

HRID 1482179 reaction equation
[CH2:1]([N:3](C(C)C)C(C)C)[CH3:2].[O:10]=[C:11]([S:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:12][C@H:13]([NH:17][C:18](=[O:23])[CH2:19][CH2:20][CH:21]=[CH2:22])[C:14]([OH:16])=[O:15].[Cl-].[NH4+]>BrCC#N>[O:10]=[C:11]([S:24][CH2:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[CH2:12][C@H:13]([NH:17][C:18](=[O:23])[CH2:19][CH2:20][CH:21]=[CH2:22])[C:14]([O:16][CH2:2][C:1]#[N:3])=[O:15]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 117735928HCID 117735928, compound

Product 1

HCID 117735204HCID 117735204, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 11534BromoacetonitrileSolvent

Procedure

N-Ethyl-N-isopropylpropan-2-amine (0.187 ml, 1.07 mmol) was added to a solution of ((S)-4-oxo-2-(pent-4-enamido)-4-(phenethylthio)butanoic acid (Compound 1f-IE) (300 mg, 0.894 mmol) in 2-bromoacetonitrile (1.87 ml), and the mixture was stirred at room temperature for 30 minutes. A saturated aqueous ammonium chloride solution (5 ml) was added to the reaction mixture, after which the mixture was extracted with ethyl acetate and the organic layer was washed with water. The organic extract was then dried over magnesium sulfate. Following concentration under reduced pressure, the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→60/40) to afford (S)-cyanomethyl 4-oxo-2-(pent-4-enamido)-4-(phenethylthio)butanoate (Compound 1g-IE) (295 mg, 88%).

Workup

  1. extractionafter which the mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with water
  3. extractionThe organic extract
  4. dry with materialwas then dried over magnesium sulfate
  5. concentrationconcentration under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→60/40)

Sources & evidence

ORD record
ord-bb431443fb134471983b35ea96a72932
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

Loading…