Iodoethane → HCID 54370181, compound

HRID 1953782Notes

Reaction equation

HRID 1953782 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([N:8]=[C:9]([O:16][CH3:17])[C:10]([O:14][CH3:15])=[N:11]2)=[C:6]([CH2:18][NH:19][C@H:20]([P:22](=[O:27])([O:25][CH3:26])[O:23][CH3:24])[CH3:21])[CH:5]=1)([O-:3])=[O:2].[CH2:28](I)[CH3:29].CCN(C(C)C)C(C)C>C(#N)C>[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([N:8]=[C:9]([O:16][CH3:17])[C:10]([O:14][CH3:15])=[N:11]2)=[C:6]([CH2:18][N:19]([CH2:28][CH3:29])[C@H:20]([P:22](=[O:27])([O:23][CH3:24])[O:25][CH3:26])[CH3:21])[CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 81531DiisopropylethylamineHCID 56993864HCID 56993864, compound

Product 1

HCID 54370181HCID 54370181, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
55 °C

Procedure

3.4 g (8.5 mmol) of dimethyl (R)-N-(7-nitro-2,3-dimethoxyquinoxalin-5-ylmethyl)-α-aminoethylphosphonate, 8.9 ml (7.5 eq.) of ethyl iodide and 20.9 ml (14.5 eq.) of Hunig's base are mixed in 18 ml of acetonitrile and stirred at 55° C. for 18 hours. The reaction mixture is evaporated and slurried with ethyl acetate. The deposited solid is filtered off and washed with ethyl acetate. The title compound is obtained in the form of a yellow resin after evaporation of the filtrate and column chromatography using ethyl acetate/methanol (95:5) as eluent.

Workup

  1. customThe reaction mixture is evaporated
  2. filtrationThe deposited solid is filtered off
  3. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-7a0a108403ab4f1c9a76169b921e4892
Source dataset
uspto-grants-2000_09
Patent number
US06117873

Reaction notes

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