HCID 67763772, compound → HCID 67763774, compound

HRID 1654461Notes

Reaction equation

HRID 1654461 reaction equation
C([O:3][P:4]([CH2:13][C@@H:14]([OH:25])[CH2:15][NH:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5])C>Cl>[ClH:24].[Cl:24][C:21]1[CH:20]=[CH:19][C:18]([CH2:17][NH:16][CH2:15][C@H:14]([OH:25])[CH2:13][P:4]([CH2:6][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)(=[O:3])[OH:5])=[CH:23][CH:22]=1

Participants

3

Reactant 1

HCID 67763772HCID 67763772, compound

Product 1

HCID 67763774HCID 67763774, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 1.80 g of (2S)-3-(p-chlorobenzylamino)-2-hydroxypropyl(benzyl)phosphinic acid ethyl ester in 30 ml of semi-concentrated hydrochloric acid is heated under reflux, a whitish suspension forming after 30 minutes. The mixture is heated under reflux for a further 20 hours and cooled to 0°, and the solid portion is filtered off, washed with water and dried under reduced pressure at 60°. Recrystallisation from aqueous methanol and drying yield 3-(p-chlorobenzylamino)-2-(2S)-hydroxypropyl(benzyl)phosphinic acid hydrochloride having a melting point of 211.5°-212°.

Workup

  1. temperatureunder reflux
  2. customa whitish suspension forming after 30 minutes
  3. temperatureThe mixture is heated
  4. temperatureunder reflux for a further 20 hours
  5. temperaturecooled to 0°
  6. filtrationthe solid portion is filtered off
  7. washwashed with water
  8. customdried under reduced pressure at 60°
  9. customRecrystallisation from aqueous methanol
  10. customdrying

Sources & evidence

ORD record
ord-bd813180951242919dfaedfb30fba3df
Source dataset
uspto-grants-1995_04
Patent number
US05407922

Reaction notes

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