HCID 67566296, compound → HCID 9821380, compound

HRID 1729193Notes

Reaction equation

HRID 1729193 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C@@H:10]([NH:12][CH2:13][C@H:14]([OH:26])[CH2:15][P:16]([CH2:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)(=[O:18])[O-:17])[CH3:11])[CH:7]=[CH:8][CH:9]=1)([OH:3])=[O:2].[Li+]>O>[C:1]([C:4]1[CH:5]=[C:6]([C@@H:10]([NH:12][CH2:13][C@H:14]([OH:26])[CH2:15][P:16]([CH2:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)(=[O:17])[OH:18])[CH3:11])[CH:7]=[CH:8][CH:9]=1)([OH:3])=[O:2]

Participants

3

Reactant 1

HCID 67566296HCID 67566296, compound

Product 1

HCID 9821380HCID 9821380, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1.0 g of lithium 3-{N-[1(S)-(3-carboxyphenyl)ethyl]amino}-2(S)-hydroxy-propyl(cyclohexylmethyl)phosphinate in 2 ml of water is applied to a DOWEX® 50 W×8 ion exchange column (40-60 mesh) and eluted with water. The ninhydrin-positive fractions are combined and concentrated to dryness by evaporation under reduced pressure. Crystallisation of the foamy residue of concentration by evaporation from ethanol/tetrahydrofuran gives 3-{N-[1(S)-(3-carboxyphenyl)ethyl]amino}-2(S)-hydroxy-propyl(cyclohexylmethyl)phosphinic acid having a melting point of 225°-228°.

Workup

  1. washeluted with water
  2. concentrationconcentrated to dryness by evaporation under reduced pressure
  3. customCrystallisation of the foamy residue of concentration
  4. customby evaporation from ethanol/tetrahydrofuran

Sources & evidence

ORD record
ord-4640086e1aaa4b838b898a917c162148
Source dataset
uspto-grants-1994_07
Patent number
US05332729

Reaction notes

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