Cyclohexylamine → decyl N-trifluoroacetyl-N-(bis(cyclohexylamino)phosphonomethyl)glycinate

HRID 2413069Notes

Reaction equation

HRID 2413069 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]([N:5]([CH2:20][P:21]([O:25]Cl)([O:23]Cl)=[O:22])[CH2:6][C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:8])=[O:4].[CH:29]1([NH2:35])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>CCOCC>[F:1][C:2]([F:28])([F:27])[C:3]([N:5]([CH2:20][P:21]([O:25][NH:35][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)([O:23][NH:35][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)=[O:22])[CH2:6][C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:8])=[O:4]

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 53672523decyl N-trifluoroacetyl-N-(dichlorophosphonomethyl)glycinate

Product 1

HCID 54141188decyl N-trifluoroacetyl-N-(bis(cyclohexylamino)phosphonomethyl)glycinate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of decyl N-trifluoroacetyl-N-(dichlorophosphonomethyl)glycinate (6.63 g, 0.015 mole) in 200 ml. of ether was added with good stirring cyclohexylamine (5.95 g, 0.06 mole) in 50 ml. of ether. The reaction was stirred overnight at room temperature, then filtered, and the filtrate concentrated in vacuo. The residue was dissolved in fresh ether, washed with water, dried over MgSO4 and concentrated in vacuo. The residue was eluted through a dry column chromatograph with ethyl acetate to yield decyl N-trifluoroacetyl-N-(bis(cyclohexylamino)phosphonomethyl)glycinate, m.p. 79.5°-82.5° C.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate concentrated in vacuo
  3. dissolutionThe residue was dissolved in fresh ether
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. washThe residue was eluted through a dry column chromatograph with ethyl acetate

Sources & evidence

ORD record
ord-25ff4916de9e495282149876b7093c2f
Source dataset
uspto-grants-1985_01
Patent number
US04496389

Reaction notes

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