Triethylamine → HCID 9805227, compound

HRID 861885Notes

Reaction equation

HRID 861885 reaction equation
[CH:1]1([C:7]2[CH:16]=[C:15]3[C:10]([CH2:11][CH2:12][C:13]([C:17](O)=[O:18])=[CH:14]3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.P(C#N)(=O)(OCC)OCC.[NH2:30][C:31]1[CH:45]=[CH:44][C:34]([CH2:35][P:36](=[O:43])([O:40][CH2:41][CH3:42])[O:37][CH2:38][CH3:39])=[CH:33][CH:32]=1.C(N(CC)CC)C>CN(C)C=O.O>[CH:1]1([C:7]2[CH:16]=[C:15]3[C:10]([CH2:11][CH2:12][C:13]([C:17]([NH:30][C:31]4[CH:32]=[CH:33][C:34]([CH2:35][P:36]([O:37][CH2:38][CH3:39])([O:40][CH2:41][CH3:42])=[O:43])=[CH:44][CH:45]=4)=[O:18])=[CH:14]3)=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 88358Diethyl p-aminobenzylphosphonateHCID 18472389HCID 18472389, compound

Product 1

HCID 9805227HCID 9805227, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution off 7-cyclohexyl-3,4-dihydronaphthalene-2-carboxylic acid (0.51 g) in N,N-dimethylformamide (DMF) (15 ml), diethyl phosphorocyanidate (DEPC) (0.36 g) was added under ice-cooling conditions, followed by stirring for 30 minutes. Diethyl 4-aminobenzylphosphonate (0.54 g) and triethylamine (0.22 g) were then added in this order, followed by stirring under ice-cooling conditions for 2 hours, after which the reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and brine, and dried (MgSO4), after which the solvent was evaporated off. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:2, v/v) to yield 7-cyclohexyl-N-(4-diethoxyphosphorylmethylphenyl)-3,4-dihydronaphthalene-2-carboxamide (0.43 g, 45%) as colorless prisms having a melting point of 137°-138° C.

Workup

  1. temperaturecooling conditions
  2. stirringby stirring under ice-
  3. temperaturecooling conditions for 2 hours
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with water and brine
  6. dry with materialdried (MgSO4)
  7. customafter which the solvent was evaporated off
  8. washeluted with ethyl acetate-hexane (1:2

Sources & evidence

ORD record
ord-54274d41f7ba469f8c2df9f8d4ec3562
Source dataset
uspto-grants-1998_02
Patent number
US05716944

Reaction notes

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