Bromoacetonitrile → HCID 89668557, compound

HRID 1482380Notes

Reaction equation

HRID 1482380 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH2:8][C@H:9]([NH:13][C:14](=[O:19])[CH2:15][CH2:16][CH:17]=[CH2:18])[C:10]([OH:12])=[O:11])[CH:5]=[CH:6][CH:7]=1.Br[CH2:21][C:22]#[N:23].CCN(C(C)C)C(C)C>CN(C=O)C>[C:22]([CH2:21][O:11][C:10](=[O:12])[C@@H:9]([NH:13][C:14](=[O:19])[CH2:15][CH2:16][CH:17]=[CH2:18])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([I:1])[CH:3]=1)#[N:23]

Participants

5

Reactant 3

HCID 11534BromoacetonitrileHCID 81531DiisopropylethylamineHCID 89668571HCID 89668571, compound

Product 1

HCID 89668557HCID 89668557, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 93d (0.494 g, 1.324 mmol) was dissolved in DMF (10 ml), and 2-bromoacetonitrile (0.63 g, 5.30 mmol) and DIPEA (0.341 g, 2.65 mmol) were slowly added at room temperature. After stirring at room temperature for 30 minutes, the reaction solution was concentrated under reduced pressure, and the resulting residue was purified by column chromatography (petroleum ether:ethyl acetate=5:1) to afford (S)-3-(3-iodo-phenyl)-2-pent-4-enoylamino-propionic acid cyanomethyl ester (Compound 93e) (0.392 g, 72%).

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. customthe resulting residue was purified by column chromatography (petroleum ether:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-412991f241b94f9699044916e967f360
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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