4-Chlorobenzylamine → HCID 67763772, compound

HRID 1654464Notes

Reaction equation

HRID 1654464 reaction equation
[CH2:1]([O:3][P:4]([CH2:13][C@@H:14]([OH:17])[CH2:15]Cl)([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5])[CH3:2].[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=1.C(N(C(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:24][CH2:23][C:22]1[CH:25]=[CH:26][C:19]([Cl:18])=[CH:20][CH:21]=1)([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 660364-ChlorobenzylamineHCID 81531DiisopropylethylamineHCID 10333694HCID 10333694, compound

Product 1

HCID 67763772HCID 67763772, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.76 g of (2R)-3-chloro-2-hydroxypropyl(benzyl)phosphinic acid ethyl ester, 3.54 g of p-chlorobenzylamine, 3.25 g of N-ethyl-N,N-diisopropylamine and 20 ml of ethanol is heated under reflux for 48 hours. Removal of the solvent and chromatography yield (2S)-3-(p-chlorobenzylamino)-2-hydroxypropyl(benzyl)phosphinic acid ethyl ester; 1H-NMR spectrum (in CDCl3): δ=7.4-7.17 (9H,m); 4.14-3.83 (3H,m); 3.71 (2H, ABq); 3.20 (2H,d): 2.6-2.5 (2H,m); 1.96-1.62 (2H,m); 1.25 (3H,t); 31P-NMR spectrum (in CDCl3): δ=53.9; 52.7.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 48 hours
  3. customRemoval of the solvent and chromatography

Sources & evidence

ORD record
ord-354863c893264d82be3828d9232c725b
Source dataset
uspto-grants-1995_04
Patent number
US05407922

Reaction notes

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