Sodium Hydroxide → HCID 13665150, compound

HRID 1638410Notes

Reaction equation

HRID 1638410 reaction equation
CS([N:5]1[CH2:9][C@@H:8]([P:10]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])[CH2:7][C@H:6]1[CH2:24][P:25]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:26])(=O)=O.[OH-].[Na+]>C1(O)C=CC=CC=1.Br>[CH:18]1([P:10]([CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)([C@@H:8]2[CH2:9][NH:5][C@H:6]([CH2:24][P:25]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[O:26])[CH2:7]2)=[O:11])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 13665146HCID 13665146, compound

Product 1

HCID 13665150HCID 13665150, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 996PhenolSolvent

Procedure

(2S,4S)-N-methanesulfonyl-4-dicyclohexylphosphinyl-2 -diphenylphosphinylmethylpyrrolidine [IX] in an amount of 350 mg was mixed with and dissolved in 700 mg of phenol and 5.3 ml of 48% hydrobromic acid, and the solution was refluxed in nitrogen atmosphere for 8-10 hours. After completion of the reaction, the solution was made alkaline with a 30% aqueous solution of caustic soda and was then extracted three times with 20 ml of ethyl acetate in each case. The extract was washed with 20 ml of water and then with 20 ml of a saturated solution of sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by way of column chromatography on silica gel whereby 196 mg (yield: 65%) of the title compound was obtained as crystals.

Workup

  1. customAfter completion of the reaction
  2. extractionwas then extracted three times with 20 ml of ethyl acetate in each case
  3. washThe extract was washed with 20 ml of water
  4. dry with materialwith 20 ml of a saturated solution of sodium chloride, dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-218f76cc00954e6abfb8d6c29bf13f81
Source dataset
uspto-grants-1989_11
Patent number
US04879389

Reaction notes

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