Hydrochloric Acid → 3-Amino-1-hydroxy-propyl(n-butyl)phosphinic acid hydrochloride

HRID 973631Notes

Reaction equation

HRID 973631 reaction equation
C(OC([NH:11][CH2:12][CH2:13][CH:14]([P:16]([CH2:21][CH2:22][CH2:23][CH3:24])(=[O:20])[O:17]CC)[OH:15])=O)C1C=CC=CC=1.O.C(O)C.[ClH:29]>>[ClH:29].[NH2:11][CH2:12][CH2:13][CH:14]([P:16]([CH2:21][CH2:22][CH2:23][CH3:24])(=[O:17])[OH:20])[OH:15]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 10450970HCID 10450970, compound

Product 1

HCID 867447623-Amino-1-hydroxy-propyl(n-butyl)phosphinic acid hydrochloride

Procedure

A suspension of 1.3 g of ethyl 3-(N-benzyloxycarbonylamino)-1-hydroxy-propyl(n-butyl)phosphinate in 10 ml of concentrated aqueous hydrochloric acid is heated to reflux for 20 hours. The clear solution is cooled to room temperature and washed with 1×50 ml of dichloromethane and 1×50 ml of ether. Evaporation of the aqueous layer affords a solid which is co-evaporated with 5×50 ml of water and 5×50 ml of absolute ethanol. Drying of the solid and crystallisation from ethanol affords 3-amino-1-hydroxy-propyl(n-butyl)phosphinic acid hydrochloride, m.p. 147°-150°. Dissolution of the hydrochloride salt in ethanol and treatment with propylene oxide affords, after filtration and drying, 3-amino-1-hydroxy-propyl(n-butyl)phosphinic acid, m.p. 123°-125°.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 20 hours
  3. washwashed with 1×50 ml of dichloromethane and 1×50 ml of ether
  4. customEvaporation of the aqueous layer
  5. customaffords a solid which
  6. dry with materialDrying of the solid and crystallisation from ethanol

Sources & evidence

ORD record
ord-488a26bca9b54969894d77f88babc92e
Source dataset
uspto-grants-1991_11
Patent number
US05064819

Reaction notes

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