Diethylamine → HCID 86742039, compound

HRID 569045Notes

Reaction equation

HRID 569045 reaction equation
[CH2:1]([O:3][P:4]([C:9]1[N:10]=[CH:11][C:12]2[NH:13][C:14]3[C:19]([C:20]=2[CH:21]=1)=[C:18]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:17]=[CH:16][CH:15]=3)(=[O:8])[O:5]CC)[CH3:2].C(Cl)(=O)C(Cl)=O.[CH2:36]([NH:38][CH2:39][CH3:40])[CH3:37]>ClCCl.C(O)(=O)C>[CH2:1]([O:3][P:4]([C:9]1[N:10]=[CH:11][C:12]2[NH:13][C:14]3[C:19]([C:20]=2[CH:21]=1)=[C:18]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:17]=[CH:16][CH:15]=3)(=[O:5])[OH:8])[CH3:2].[CH2:36]([N-:38][CH2:39][CH3:40])[CH3:37]

Participants

6

Reactant 3

HCID 8021DiethylamineHCID 65578Oxalyl chlorideHCID 13316805HCID 13316805, compound

Product 1

HCID 86742039HCID 86742039, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.2 g of 5-benzyloxy-β-carboline-3-phosphonic acid diethyl ester (example 61) and 0.1 g of oxalyl chloride in 10 ml of dichloromethane is stirred for 24 hours at room temperature and then mixed with an excess of diethylamine. It is heated to boiling for 2 more hours for completion of the reaction. It is diluted with acetic acid and extracted with water. The evaporation residue of the organic phase yields 0.15 g of the title compound after crystallization from tetrahydrofuran.

Workup

  1. temperatureIt is heated
  2. customto boiling for 2 more hours for completion of the reaction
  3. extractionextracted with water

Sources & evidence

ORD record
ord-0644e58133d8430285fc7b778fdd087d
Source dataset
uspto-grants-1988_03
Patent number
US04731358

Reaction notes

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