Triethylamine → HCID 67387964, compound

HRID 912601Notes

Reaction equation

HRID 912601 reaction equation
[CH3:1]/[CH:2]=[C:3]1\[C@H:4]2[CH:11]=[C:10]([CH3:12])[CH2:9][C@@:8]\1([NH2:13])[C:7]1[CH:14]=[CH:15][C:16]([NH:18][C:6]=1[CH2:5]2)=[O:17].C(N(CC)CC)C.[C:26](Cl)(=[O:30])[O:27][CH2:28][CH3:29]>C1COCC1>[CH2:28]([O:27][C:26]([NH:13][C@@:8]12[C:7]3[CH:14]=[CH:15][C:16](=[O:17])[NH:18][C:6]=3[CH2:5][C@@H:4](/[C:3]/1=[CH:2]\[CH3:1])[CH:11]=[C:10]([CH3:12])[CH2:9]2)=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 9794806HCID 9794806, compound

Product 1

HCID 67387964HCID 67387964, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Dissolved 10 mg huperzine A and 10 mg triethylamine in 5 mL dry THF; cooled the solution down to 0° C.; added ethyl chlorocarbonate (6 mg) and stirred the resultant reaction mixture for 4 hours; filtered to remove solid residues; after concentrating the filtrate, purified on prep TLC (chloroform:methanol=9:1) to yield 8 mg of pure title compound. MS: 315 (M+1).

Workup

  1. customreaction mixture for 4 hours
  2. filtrationfiltered
  3. customto remove solid residues
  4. concentrationafter concentrating the filtrate
  5. custompurified on prep TLC (chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-1e8b0eb5811044b0aa6772d2aeac3e17
Source dataset
uspto-grants-2011_09
Patent number
US08026251B2

Reaction notes

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