Diisopropylethylamine → HCID 54145704, compound

HRID 1440684Notes

Reaction equation

HRID 1440684 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].[Cl:18][C:19]1[CH:20]=[C:21]([CH:26]([NH2:28])[CH3:27])[CH:22]=[CH:23][C:24]=1[Cl:25].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:21]1[CH:22]=[CH:23][C:24]([Cl:25])=[C:19]([Cl:18])[CH:20]=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 31592421-(3,4-dichlorophenyl)ethanamineHCID 103790613-chloro-2(R)-hydroxy-propyl(cyclohexylmethyl)phosphinic acid ethyl ester

Product 1

HCID 54145704HCID 54145704, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4.24 g of 3-chloro-2(R)-hydroxy-propyl-(cyclohexylmethyl)-phosphinic acid ethyl ester, 2.85 g of 1-(3,4-dichlorophenyl)ethylamine, 1.95 g of Hunig base and 15 ml of ethanol is heated at reflux for 4 days. After cooling to room temperature and removal of the solvent under reduced pressure, the reaction mixture is partitioned between dichloro-methane and water, dried over sodium sulfate and again concentrated to dryness by evaporation. Chromatography on silica gel yields 3-{N-[1-(3,4-dichlorophenyl)ethyl]amino}-2(S)-hydroxy-propyl(cyclohexylmethyl)phosphinic acid ethyl ester, [α]20D =-1.8°±0.9° (c=1.079 in chloroform).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 4 days
  3. customremoval of the solvent under reduced pressure
  4. customthe reaction mixture is partitioned between dichloro-methane and water
  5. dry with materialdried over sodium sulfate
  6. concentrationagain concentrated to dryness by evaporation

Sources & evidence

ORD record
ord-69d66983987c429489cde726c2f75842
Source dataset
uspto-grants-1996_03
Patent number
US05500418

Reaction notes

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