Hydrochloric Acid → HCID 9890651, compound

HRID 259907Notes

Reaction equation

HRID 259907 reaction equation
Cl.[CH2:2]([N:9]([C@H:17]([C@@H:25]([OH:39])[CH2:26][C@@H:27]([NH:35]C(=O)C)[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+]>C(O)CCC>[CH2:2]([N:9]([C@H:17]([C@@H:25]([OH:39])[CH2:26][C@@H:27]([NH2:35])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57020529HCID 57020529, compound

Product 1

HCID 9890651HCID 9890651, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To 40 ml of 4N hydrochloric acid, was added 10.86 g of (2S,3S,5S)-2-(N,N-dibenzylamino)-5-acetylamino-1,6-diphenyl-3-hexanol, and the resulting solution was refluxed for 6 hours and cooled to room temperature. To the reaction mixture, was added 30 ml of n-butanol, and the resulting mixture was neutralized with dropwise addition of a 10% solution of sodium hydroxide. The organic layer of n-butanol was separated, washed with water, dried over sodium sulfate and concentrated to dryness under reduced pressure, thereby obtaining 9.29 g (100%) of the title compound as a colorless resin. This compound was found to be a single compound by high performance liquid chromatography (HPLC), and hence used in the subsequent process without further purification.

Workup

  1. temperaturethe resulting solution was refluxed for 6 hours
  2. customThe organic layer of n-butanol was separated
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-2c36f84edc0742468fb391c07244e732
Source dataset
uspto-grants-1996_06
Patent number
US05523458

Reaction notes

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