Acetyl chloride → HCID 44358184, compound

HRID 322104Notes

Reaction equation

HRID 322104 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([N:10]3[CH2:14][CH2:13][C@H:12]([NH2:15])[CH2:11]3)[C:4]=2[CH2:3][CH2:2]1.C(N(CC)CC)C.[C:23](Cl)(=[O:25])[CH3:24]>C(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([N:10]3[CH2:14][CH2:13][C@H:12]([NH:15][C:23](=[O:25])[CH3:24])[CH2:11]3)[C:4]=2[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 69830457HCID 69830457, compound

Product 1

HCID 44358184HCID 44358184, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-N-(2,3-dihydrobenzofuran-4-yl)-3-(amino)pyrrolidine (0.1 mmol) and triethylamine (0.15 mmol) were dissolved in CH2Cl2. Acetylchloride (0.12 mmol) was added, and the reaction was stirred at room temperature for 16 hours. The organics were then washed with 1 N HCl, NaHCO3, and brine. The organic solution was dried over sodium sulfate, concentrated in vacuo, and purified by silica gel column chromatography eluting with 4% methanol in CH2Cl2 to yield the title compound.

Workup

  1. washThe organics were then washed with 1 N HCl, NaHCO3, and brine
  2. dry with materialThe organic solution was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. custompurified by silica gel column chromatography
  5. washeluting with 4% methanol in CH2Cl2

Sources & evidence

ORD record
ord-e6a725c97224444daa78caa1d0ac8766
Source dataset
uspto-grants-2001_04
Patent number
US06211225B1

Reaction notes

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