Triethylamine → HCID 18794251, compound

HRID 1004049Notes

Reaction equation

HRID 1004049 reaction equation
[CH3:1][C:2]1[NH:16][CH2:15][CH2:14][C:4]2=[C:5]3[C:10](=[N:11][C:3]=12)[CH:9]=[CH:8][C:7]([O:12][CH3:13])=[CH:6]3.C(N(CC)CC)C.Cl[C:25]([O:27][CH2:28][CH3:29])=[O:26]>ClCCl>[CH2:1]=[C:2]1[C:3]2[NH:11][C:10]3[C:5](=[CH:6][C:7]([O:12][CH3:13])=[CH:8][CH:9]=3)[C:4]=2[CH2:14][CH2:15][N:16]1[C:25]([O:27][CH2:28][CH3:29])=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 178487038HCID 178487038, compound

Product 1

HCID 18794251HCID 18794251, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 10-methoxyharmalan in dichloro-methane is added triethylamine (1.5 eq) and the mixture is cooled to 0° C. A solution (1/5 v/v) of ethyl chloro-formate in dichloromethane is then added dropwise. The mixture is stirred at 0° C. until the starting material disappears (2 h). After evaporation of the solvent, the crude product is separated out on a chromatography plate (eluent: EtOAc/pet. ether; 50/50).

Workup

  1. custom(2 h)
  2. customAfter evaporation of the solvent
  3. customthe crude product is separated out on a chromatography plate (eluent: EtOAc/pet. ether; 50/50)

Sources & evidence

ORD record
ord-f5fdb552537747b6af0f5e7b9a92e04b
Source dataset
uspto-grants-2000_04
Patent number
US06048868

Reaction notes

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