Diethyl Ether → HCID 54285057, compound

HRID 2413725Notes

Reaction equation

HRID 2413725 reaction equation
N[C@H](C(N1CCC[C@H]1C(N1CCC[C@H]1C(O)=O)=O)=O)C.[CH2:21]([S:28]([NH:31][C@H:32]([C:34]([N:36]1[CH2:50][CH2:49][CH2:48][C@H:37]1[C:38]([N:40]1[CH2:47][CH2:46][CH2:45][C@H:41]1[C:42]([OH:44])=[O:43])=[O:39])=[O:35])[CH3:33])(=[O:30])=[O:29])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(S(Cl)(=O)=O)C1C=CC=CC=1.CCOCC>[OH-].[Na+]>[CH2:21]([S:28]([NH:31][C@H:32]([C:34]([N:36]1[CH2:50][CH2:49][CH2:48][C@H:37]1[C:38]([N:40]1[CH2:47][CH2:46][CH2:45][C@H:41]1[C:42]([OH:44])=[O:43])=[O:39])=[O:35])[CH3:33])(=[O:30])=[O:29])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 74740Phenylmethanesulfonyl chlorideHCID 70414828HCID 70414828, compound

Product 1

HCID 54285057HCID 54285057, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

N-benzylsulfonyl-L-alanyl-L-prolyl-L-proline N-alanyl-L-prolyl-L-proline (3.00 g, 10.6 m mole) was dissolved in 1N aqueous sodium hydroxide (21.2 ml, 21.2 m mole), and benzylsulfonylchloride (2.02 g, 10.6 m mole)-ether (10 ml) solution was added dropwise thereto while stirring and cooling with ice over 15 minutes. Thus obtained reaction solution was further stirred for 3 hours at room temperature, and the ether layer was separated. The water layer was washed with ether (10 ml) again. The water layer was mixed with ethyl acetate (20 ml), and then adjusted to pH 1.0 with 6N hydrochloric acid while stirring. The ethyl acetate layer was separated, and the water layer was further extracted with ethyl acetate (20 ml). The ethyl acetate layers were combined and washed with 10% aqueous sodium chloride (20 ml), and dried over anhydrous sodium sulfate. The ethyl acetate was removed by distillation under reduced pressure therefrom. Ether was added to the syrupy residue as produced above to effect crystallization. The thus produced crystals were obtained by filtration and washed sufficiently with ether, and dried under reduced pressure to give white crystals of N-benzylsulfonyl-L-alanyl-L-prolyl-L-proline (1.41 g).

Workup

  1. temperaturecooling with ice over 15 minutes
  2. customThus obtained reaction solution
  3. stirringwas further stirred for 3 hours at room temperature
  4. customthe ether layer was separated
  5. washThe water layer was washed with ether (10 ml) again
  6. additionThe water layer was mixed with ethyl acetate (20 ml)
  7. stirringwhile stirring
  8. customThe ethyl acetate layer was separated
  9. extractionthe water layer was further extracted with ethyl acetate (20 ml)
  10. washwashed with 10% aqueous sodium chloride (20 ml)
  11. dry with materialdried over anhydrous sodium sulfate
  12. customThe ethyl acetate was removed by distillation under reduced pressure
  13. additionEther was added to the syrupy residue
  14. customas produced above
  15. customcrystallization
  16. customThe thus produced crystals were obtained by filtration
  17. washwashed sufficiently with ether
  18. customdried under reduced pressure

Sources & evidence

ORD record
ord-9c64399eb3de4eb89ee3183183f9002b
Source dataset
uspto-grants-1988_01
Patent number
US04719200

Reaction notes

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