Water → HCID 18652783, compound

HRID 1440689Notes

Reaction equation

HRID 1440689 reaction equation
[OH-].[Li+].O.C([O:6][P:7]([CH2:16][C@@H:17]([OH:29])[CH2:18][NH:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=1)([CH:9]([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])=[O:8])C.P(=O)(O)(O)O>C(O)C>[Cl:28][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][C:24]=1[Cl:27])[CH2:20][NH:19][CH2:18][C@H:17]([OH:29])[CH2:16][P:7]([CH:9]([O:10][CH2:11][CH3:12])[O:13][CH2:14][CH3:15])(=[O:6])[OH:8]

Participants

6

Reactant 4

HCID 962WaterHCID 1004Phosphoric AcidHCID 3939Lithium HydroxideHCID 54397801HCID 54397801, compound

Product 1

HCID 18652783HCID 18652783, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.254 g of lithium hydroxide and 6 ml of water are added to a solution of 2.26 g of 3-[N-(3,4-dichlorobenzyl)amino]-2(S)-hydroxy-propyl(diethoxymethyl)phosphinic acid ethyl ester in 3 ml of ethanol and the mixture is stirred at 60° for 24 hours. The mixture is allowed to cool to room temperature, adjusted to pH 7 with aqueous phosphoric acid and concentrated to dryness by evaporation. The evaporation residue is made into a slurry in hot methanol and filtered. The filtrate is concentrated to dryness by evaporation and the glassy evaporation residue is taken up in a small amount of ethanol. The pH value is adjusted to pH 1 with ethanolic hydrochloric acid and the solvent is removed. Crystallisation from acetonitrile yields 3-[N-(3,4-dichlorobenzyl)amino]-2(S)-hydroxy-propyl(diethoxymethyl)phosphinic acid; [α]20D =-10.8°±1.7° (c=0.595 in methanol); 1H-NMR (CD3OD): δ=7.76 (1H, m), 7.61 (1H, m), 7.45 (1H, m), 4.47 (1H, d), 4.29 (1H, m), 4.20 (2H, m), 3.80 (2H, m), 3.69 (2H, m), 3.25 (1H, dd), 3.02 (1H, d, d), 2.04 (1H, dd), 1.87 (1H, d, d); 1.20 (6H, t).

Workup

  1. concentrationconcentrated to dryness by evaporation
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated to dryness by evaporation
  4. customthe solvent is removed
  5. customCrystallisation from acetonitrile

Sources & evidence

ORD record
ord-3040f7b0e6304d6f9eb2f5e021ebbecd
Source dataset
uspto-grants-1996_03
Patent number
US05500418

Reaction notes

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