lithium 3-{N-[1 (R)-(3-carboxyphenyl)ethyl]amino}-2(S)-hydroxy-propyl(cyclohex-3-enylmethyl)phosphinate → HCID 67565923, compound

HRID 1729192Notes

Reaction equation

HRID 1729192 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][CH:23]=[CH:22][CH2:21]2)(=[O:18])[O-:17])[CH3:11])[CH:7]=[CH:8][CH:9]=1)([OH:3])=[O:2].[Li+:27]>C(O)C.[Pd]>[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])[O-:18])[CH3:11])[CH:7]=[CH:8][CH:9]=1)([OH:3])=[O:2].[Li+:27]

Participants

4

Reactant 1

HCID 67566287lithium 3-{N-[1 (R)-(3-carboxyphenyl)ethyl]amino}-2(S)-hydroxy-propyl(cyclohex-3-enylmethyl)phosphinate

Product 1

HCID 67565923HCID 67565923, 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 lithium 3-{N-[1(R)-(3-carboxyphenyl)ethyl]amino}-2(S)-hydroxy-propyl(cyclohex-3-enylmethyl)phosphinate in 5 ml of ethanol and the batch is hydrogenated at room temperature and normal pressure for 15 minutes. The catalyst is filtered off through Celite® and the filtrate is adjusted to a pH of 1 with ethanolic hydrochloric acid. Removal of the solvent and recrystallisation from isopropanol gives lithium 3-{N-[1(R)-(3-carboxyphenyl)ethyl]amino}-2(S)-hydroxy-propyl(cyclohexylmethyl)phosphinate, which is identical with the compound of Example 5(f).

Workup

  1. customis hydrogenated at room temperature
  2. filtrationThe catalyst is filtered off through Celite®
  3. customRemoval of the solvent and recrystallisation from isopropanol

Sources & evidence

ORD record
ord-c44d03b8a84343efb9cf512d744c3afa
Source dataset
uspto-grants-1994_07
Patent number
US05332729

Reaction notes

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