HCID 18652786, compound → HCID 6540749, compound

HRID 1440686Notes

Reaction equation

HRID 1440686 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([NH:11][CH2:12][C@H:13]([OH:25])[CH2:14][P:15]([CH2:18][CH:19]2[CH2:24][CH2:23][CH:22]=[CH:21][CH2:20]2)(=[O:17])[OH:16])[CH3:10])[CH:5]=[CH:6][C:7]=1[Cl:8]>C(O)C.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([NH:11][CH2:12][C@H:13]([OH:25])[CH2:14][P:15]([CH2:18][CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)(=[O:16])[OH:17])[CH3:10])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 1

HCID 18652786HCID 18652786, compound

Product 1

HCID 6540749HCID 6540749, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

20 mg of 5% palladium-on-carbon are added to a solution of 0.125 g of 3-{N-[1-(3,4-dichlorophenyl)ethyl]amino}-2(S)-hydroxy-propyl-(cyclohex-3-enylmethyl)-phosphinic acid in 5 ml of ethanol and hydrogenated at room temperature and normal pressure for 15 minutes. The catalyst is filtered off through Celite® and the filtrate is adjusted to pH 1 with ethanolic hydrochloric acid. Removal of the solvent and recrystallisation from isopropanol yield 3-{N-[1-(3,4-dichlorophenyl)ethyl]amino}-2(S)-hydroxy-propyl-(cyclohexylmethyl)-phosphinic acid, m.p. 173°-178°.

Workup

  1. filtrationThe catalyst is filtered off through Celite®
  2. customRemoval of the solvent and recrystallisation from isopropanol

Sources & evidence

ORD record
ord-f2c0d85c410b4c3d967668bb8b6933af
Source dataset
uspto-grants-1996_03
Patent number
US05500418

Reaction notes

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