18-Crown-6 → HCID 53912688, compound

HRID 487232Notes

Reaction equation

HRID 487232 reaction equation
[C:1]1([O:7][P:8]([CH2:17][NH:18][C@@H:19]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:31][CH:30]=2)[C:20]([NH:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[O:21])([O:10][C:11]2C=CC=CC=2)=[O:9])C=CC=CC=1.[F-].[K+].C1OCCOCCOCCOCCOCCOC1>CO>[CH3:1][O:7][P:8]([CH2:17][NH:18][C@@H:19]([CH2:28][C:29]1[CH:30]=[CH:31][C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:33][CH:34]=1)[C:20]([NH:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[O:21])([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 132812Cgs 25462HCID 522689Potassium Fluoride

Product 1

HCID 53912688HCID 53912688, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of (S)-N-[2-(diphenylphosphonomethylamino)-3-(4-biphenylyl)-propionyl]-3-aminopropionic acid (10.8 g, 19.3 mmol) in methanol (150 mL) is added potassium fluoride (11.2 g, 193 mmol) followed by 18-crown-6 (100 mg, 0.38 mmol). The solution is refluxed for 7 minutes in a preheated oil bath then stirred at room temperature for 3 hours. The volume is then reduced to 50 mL by evaporation under reduced pressure. The solution is cooled in an ice bath and treated with 2N hydrochloric acid (55 mL) and water (50 mL). The product is extracted with methylene chloride (3×70 mL). The organic layer is washed with brine then dried over sodium sulfate. The solution is filtered and concentrated in vacuo. The residue is crystallized from ether to give (S)-N-[2-(dimethylphosphonomethylamino)-3-(4-biphenylyl)-propionyl]-3-aminopropionic acid m.p. 122°-123°, [α]D =-10.56° (c=0.86, CH3OH).

Workup

  1. temperatureThe solution is refluxed for 7 minutes in a preheated oil bath
  2. customThe volume is then reduced to 50 mL by evaporation under reduced pressure
  3. temperatureThe solution is cooled in an ice bath
  4. additiontreated with 2N hydrochloric acid (55 mL) and water (50 mL)
  5. extractionThe product is extracted with methylene chloride (3×70 mL)
  6. washThe organic layer is washed with brine
  7. dry with materialthen dried over sodium sulfate
  8. filtrationThe solution is filtered
  9. concentrationconcentrated in vacuo
  10. customThe residue is crystallized from ether

Sources & evidence

ORD record
ord-24081853a0d5468294eabcb41d3dcf4f
Source dataset
uspto-grants-1994_03
Patent number
US05294632

Reaction notes

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