Triethylamine → HCID 89668552, compound

HRID 1482379Notes

Reaction equation

HRID 1482379 reaction equation
[NH2:1][C@@H:2]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([I:16])=[CH:12][CH:11]=1)[C:3]([O:5][CH2:6][C:7]#[N:8])=[O:4].C(N(CC)CC)C.[C:24](Cl)(=[O:29])[CH2:25][CH2:26][CH:27]=[CH2:28]>ClCCl>[I:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][C@H:2]([NH:1][C:24](=[O:29])[CH2:25][CH2:26][CH:27]=[CH2:28])[C:3]([O:5][CH2:6][C:7]#[N:8])=[O:4])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 42284934-Pentenoyl chlorideHCID 69049094HCID 69049094, compound

Product 1

HCID 89668552HCID 89668552, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(S)-Cyanomethyl 2-amino-3-(4-iodophenyl)propanoate (0.65 g, 1.78 mmol) was dissolved in dichloromethane (25.0 ml) under a nitrogen atmosphere, and triethylamine (0.45 g, 4.45 mmol) was added dropwise under ice-cooling. A solution of pent-4-enoyl chloride (0.25 g, 2.14 mmol) in dichloromethane (25.0 ml) was then added dropwise under ice-cooling, and the mixture was stirred at room temperature for 2.5 hours. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified by column chromatography (petroleum ether:ethyl acetate=50:50-33:67) to afford (S)-cyanomethyl 3-(4-iodophenyl)-2-(pent-4-enamido)propanoate (Compound 92) (0.57 g, 78%).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. customthe resulting residue was purified by column chromatography (petroleum ether:ethyl acetate=50:50-33:67)

Sources & evidence

ORD record
ord-68d4c73c9e204faf970586c763700d85
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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