Hydrochloric Acid → (SR)-4-{2-[2-Hydroxy-3-(4-hydroxy-3-hydroxymethylphenoxy)propylamino]propyl}phenoxymethyl(3-benzyloxypropyl)phosphinic acid, hydrochloride salt

HRID 1547Notes

Reaction equation

HRID 1547 reaction equation
[OH:1][CH:2]([CH2:34][O:35][C:36]1[CH:41]=[CH:40][C:39]([OH:42])=[C:38]([CH2:43][OH:44])[CH:37]=1)[CH2:3][NH:4][CH:5]([CH3:33])[CH2:6][C:7]1[CH:32]=[CH:31][C:10]([O:11][CH2:12][P:13]([CH2:20][CH2:21][CH2:22][O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:19])[O:14]CCCC)=[CH:9][CH:8]=1.[ClH:45]>>[ClH:45].[OH:1][CH:2]([CH2:34][O:35][C:36]1[CH:41]=[CH:40][C:39]([OH:42])=[C:38]([CH2:43][OH:44])[CH:37]=1)[CH2:3][NH:4][CH:5]([CH3:33])[CH2:6][C:7]1[CH:32]=[CH:31][C:10]([O:11][CH2:12][P:13]([CH2:20][CH2:21][CH2:22][O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:14])[OH:19])=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 131720551HCID 131720551, compound

Product 1

HCID 131720550(SR)-4-{2-[2-Hydroxy-3-(4-hydroxy-3-hydroxymethylphenoxy)propylamino]propyl}phenoxymethyl(3-benzyloxypropyl)phosphinic acid, hydrochloride salt

Procedure

The title compound was prepared from (SR)-4-{2-[2-hydroxy-3-(4-hydroxy-3-hydroxymethylphenoxy)propylamino]propyl}phenoxymethyl(3-benzyloxypropyl)phosphinic acid, n-butyl ester according to a modification of the procedure described in Example 5. Acidification to pH 3.5 with 1M hydrochloric acid followed by C18 reverse phase chromatography, eluting with water-methanol (30%) and freeze drying of the resultant foam gave the title compound as a solid.

Workup

  1. washeluting with water-methanol (30%)
  2. customfreeze drying of the resultant foam

Sources & evidence

ORD record
ord-53f0eba6f5424c5d8afd83daf49ced93
Source dataset
uspto-grants-1998_03
Patent number
US05726165

Reaction notes

Loading…