Diisopropylethylamine → 3-{N-[1-(3-cyanophenyl)ethyl]amino}-2(S)-hydroxy-propyl(cyclohexylmethyl)phosphinic acid ethyl ester

HRID 21778Notes

Reaction equation

HRID 21778 reaction equation
[CH2:1]([O:3][P:4]([CH2:13][C@@H:14]([OH:17])[CH2:15]Cl)([CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:5])[CH3:2].[C:18]([C:20]1[CH:21]=[C:22]([CH:26]([NH2:28])[CH3:27])[CH:23]=[CH:24][CH:25]=1)#[N:19].CCN(C(C)C)C(C)C>C(O)C>[CH2:1]([O:3][P:4]([CH2:13][C@@H:14]([OH:17])[CH2:15][NH:28][CH:26]([C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([C:18]#[N:19])[CH:21]=1)[CH3:27])([CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 103790613-chloro-2(R)-hydroxy-propyl(cyclohexylmethyl)phosphinic acid ethyl esterHCID 152822873-(1-Aminoethyl)benzonitrile

Product 1

HCID 152822883-{N-[1-(3-cyanophenyl)ethyl]amino}-2(S)-hydroxy-propyl(cyclohexylmethyl)phosphinic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5.65 g of 3-chloro-2(R)-hydroxy-propyl(cyclohexylmethyl)phosphinic acid ethyl ester, 2.92 g of N-[1-(3-cyanophenyl)ethyl]amine, 2.60 g of Hunig base and 10 ml of ethanol is heated under reflux for 5 days, then cooled to room temperature and concentrated by evaporation. Chromatography of the residue on silica gel gives 3-{N-[1 -(3cyanophenyl)ethyl]amino}-2(S)-hydroxy-propyl(cyclohexylmethyl)phosphinic acid ethyl ester in the form of an oil; [α}20D =+8.6 0.8 (c=1.225 in trichloromethane).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 5 days
  3. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-daea0e4a5f884fb39edf4aa3b2432bf7
Source dataset
uspto-grants-1995_06
Patent number
US05424441

Reaction notes

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