Acetaldehyde → HCID 23499496, compound

HRID 1836332Notes

Reaction equation

HRID 1836332 reaction equation
Cl.C([O:4][C:5](=[O:9])[CH2:6][CH2:7][NH2:8])C.CC[N:12]([CH2:15][CH3:16])CC.[CH:17](=O)[CH3:18].[Si](C#N)(C)(C)[CH3:21]>C(Cl)Cl>[CH2:17]([CH:6]([CH2:7][NH:8][CH:16]([C:15]#[N:12])[CH3:21])[C:5]([OH:4])=[O:9])[CH3:18]

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 458475beta-Alanine, ethyl ester, hydrochloride

Product 1

HCID 23499496HCID 23499496, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of β-alanine ethyl ester hydrochloride (3.23 g, 0.021 mol) in DCM (80 mL) is added Et3N (3.0 mL, 0.021 mol). The resulting mixture is stirred at room temperature for 10 minutes, then acetaldehyde (1.2 mL, 0.021 mol) is added, followed by the drop-wise addition of TMSCN (2.86 mL, 0.021 mol). The resulting mixture is stirred at room temperature for about 18 hours, then is diluted with DCM (100 mL) and is washed with brine (100 mL), dried (Na2SO4), and concentrated in vacuo. The crude mixture is purified by flash column chromatography on silica gel (7:3 EtOAc/hexane). The title compound is isolated as its hydrochloride salt.

Workup

  1. stirringThe resulting mixture is stirred at room temperature for about 18 hours
  2. washis washed with brine (100 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude mixture is purified by flash column chromatography on silica gel (7:3 EtOAc/hexane)

Sources & evidence

ORD record
ord-abe604fbcd7546079262c8924701db23
Source dataset
uspto-grants-2004_08
Patent number
US06777431B2

Reaction notes

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