Hydrochloric Acid → 3-Amino-2-hydroxy-propyl(ethyl)phosphinic acid hydrochloride

HRID 1612706Notes

Reaction equation

HRID 1612706 reaction equation
C1(=O)[N:5]([CH2:6][CH:7]([O:16][Si](C)(C)C)[CH2:8][P:9]([CH2:14][CH3:15])(=[O:13])[O:10]CC)C(=O)C2=CC=CC=C12.[ClH:27]>>[ClH:27].[NH2:5][CH2:6][CH:7]([OH:16])[CH2:8][P:9]([CH2:14][CH3:15])(=[O:10])[OH:13]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 19090885Ethyl 3-phthalimido-2-trimethylsilyloxy-propyl(ethyl)phosphinate

Product 1

HCID 856311253-Amino-2-hydroxy-propyl(ethyl)phosphinic acid hydrochloride

Procedure

A solution of 6.4 g of ethyl 3-phthalimido-2-trimethylsilyloxy-propyl(ethyl)phosphinate in 100 ml of concentrated aqueous hydrochloric acid is heated to reflux for 20 hours. After this time the suspension is cooled to room temperature and filtered. The filtrate is evaporated to dryness, the resulting semi-solid is co-evaporated with water (5×50 ml) and absolute ethanol (5×100 ml) and the white solid is dried in high vacuum overnight. Crystallisation from absolute ethanol/acetone affords 3-amino-2-hydroxy-propyl(ethyl)phosphinic acid hydrochloride, m.p. 114°-115°.

Workup

  1. temperatureto reflux for 20 hours
  2. filtrationfiltered
  3. customThe filtrate is evaporated to dryness
  4. customthe white solid is dried in high vacuum overnight
  5. customCrystallisation from absolute ethanol/acetone

Sources & evidence

ORD record
ord-fabb741967044524968f38e3208d24f6
Source dataset
uspto-grants-1993_03
Patent number
US05190933

Reaction notes

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