Propylene Oxide → 3-Amino-2-(4-chlorophenyl)-1-hydroxy-propyl(methyl)phosphinic acid

HRID 1463638Notes

Reaction equation

HRID 1463638 reaction equation
C(OC([NH:8][CH2:9][CH:10]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)[CH:11]([P:13]([CH3:18])(=[O:17])[O:14]CC)[OH:12])=O)(C)(C)C.C1OC1C>Cl.CO>[NH2:8][CH2:9][CH:10]([C:19]1[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=1)[CH:11]([P:13]([CH3:18])(=[O:14])[OH:17])[OH:12]

Participants

5

Reactant 2

HCID 6378Propylene OxideHCID 19090866HCID 19090866, compound

Product 1

HCID 99432103-Amino-2-(4-chlorophenyl)-1-hydroxy-propyl(methyl)phosphinic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 0.64 g of ethyl 3-(N-tert.-butyloxycarbonylamino)-2-(4-chlorophenyl)-1-hydroxy-propyl(methyl)phosphinate in 12 ml of concentrated aqueous hydrochloric acid is heated to reflux for 5 hours. The mixture is then cooled and evaporated to dryness in vacuo. The residue is repeatedly co-evaporated with methanol until the hydrochloride salt is obtained as a foam. This is dissolved in 50 ml of methanol and treated with 25 ml of propylene oxide after 40 minutes stirring at room temperature a solid precipitates, and the suspension stirred for a further 11/2 hours. The solid is collected by filtration washed with propylene oxide and ether and dried the solid is redissolved in methanol at elevated temperature and filtered. Concentration in vacuo and dilution with ether affords a solid which is collected and dried to give 3-amino-2-(4-chlorophenyl)-1-hydroxy-propyl(methyl)phosphinic acid, m.p. 240°-241° C.

Workup

  1. temperatureto reflux for 5 hours
  2. temperatureThe mixture is then cooled
  3. customevaporated to dryness in vacuo
  4. customis obtained as a foam
  5. customprecipitates
  6. stirringthe suspension stirred for a further 11/2 hours
  7. filtrationThe solid is collected by filtration
  8. washwashed with propylene oxide and ether
  9. customdried the solid
  10. dissolutionis redissolved in methanol at elevated temperature
  11. filtrationfiltered
  12. concentrationConcentration in vacuo and dilution with ether
  13. customaffords a solid which
  14. customis collected
  15. customdried

Sources & evidence

ORD record
ord-04e12f3c6e7b4367a79f44ae2af0071f
Source dataset
uspto-grants-1994_04
Patent number
US05300679

Reaction notes

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