Benzenemethanamine, 3,4-dichloro- → HCID 54397801, compound

HRID 1492976Notes

Reaction equation

HRID 1492976 reaction equation
[CH2:1]([O:3][P:4]([CH2:13][C@@H:14]([OH:17])[CH2:15]Cl)([CH:6]([O:10][CH2:11][CH3:12])[O:7][CH2:8][CH3:9])=[O:5])[CH3:2].CCN(C(C)C)C(C)C.[Cl:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=1[Cl:36])[CH2:31][NH2:32]>C(O)C>[CH2:1]([O:3][P:4]([CH2:13][C@@H:14]([OH:17])[CH2:15][NH:32][CH2:31][C:30]1[CH:33]=[CH:34][C:35]([Cl:36])=[C:28]([Cl:27])[CH:29]=1)([CH:6]([O:10][CH2:11][CH3:12])[O:7][CH2:8][CH3:9])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 1608Benzenemethanamine, 3,4-dichloro-HCID 81531DiisopropylethylamineHCID 11778884HCID 11778884, compound

Product 1

HCID 54397801HCID 54397801, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 7.2 g of 3-chloro-2(R)-hydroxy-propyl-(diethoxymethyl)phosphinic acid ethyl ester, 3.6 g of Hunig base and 6.5 g of 3,4-dichlorobenzylamine in 20 ml of anhydrous ethanol is heated at reflux for 4 days. The mixture is concentrated to dryness by evaporation and the residue is partitioned between dichloromethane and water. The organic phase is separated off, dried over sodium sulfate, concentrated by evaporation and purified by chromatography on silica gel, yielding 3-[N-(3,4-dichlorobenzyl)amino]-2(S)-hydroxy-propyl(diethoxymethyl)phosphinic acid ethyl ester in the form of a yellowish oil; 1H-NMR (CD3Cl3 /D2O): δ=7.43 (1H,m,phenyl), 7.39 (1H,m,phenyl), 7.15 (1H,m,phenyl), 4.70 (1H,s,CHP), 4.20 (3H,m,CHO+CH2OP), 3.83 (2H,m, CH2OC), 3.70 (4H,m,CH2 phenyl+CH2OC), 2.65 (2H,m,CH2N), 2.20-1.71 (2H,m, CH2P), 1.40-1.26 (6H,m, 3×CH3).

Workup

  1. temperatureat reflux for 4 days
  2. concentrationThe mixture is concentrated to dryness by evaporation
  3. customthe residue is partitioned between dichloromethane and water
  4. customThe organic phase is separated off
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated by evaporation
  7. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-9297a07471664885a3561cf18769073f
Source dataset
uspto-grants-1994_12
Patent number
US05376684

Reaction notes

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