Hydrochloric Acid → HCID 14858830, compound

HRID 1073982Notes

Reaction equation

HRID 1073982 reaction equation
[NH2:1][C@H:2]([C:4]([N:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5])[CH3:3].[C:14]1([S:24](Cl)(=[O:26])=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1.O.Cl>[OH-].[Na+].O1CCOCC1>[C:14]1([S:24]([NH:1][C@H:2]([C:4]([N:6]2[CH2:13][CH2:12][CH2:11][C@H:7]2[C:8]([OH:10])=[O:9])=[O:5])[CH3:3])(=[O:26])=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 665601-Naphthalenesulfonyl chlorideHCID 83525L-Alanyl-L-proline

Product 1

HCID 14858830HCID 14858830, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

L-alanyl-L-proline (1.86 g, 10 mmole) was dissolved in 1N aqueous sodium hydroxide (10 ml)-dioxane (5 ml), and dioxane (5 ml) solution of α-naphthalenesulfonylchloride (2.26 g, 10 mmole) was added dropwise to the solution while cooling with ice and stirring while keeping pH value thereof to between 10 and 11 with 1N aqueous sodium hydroxide. After the addition, the mixture was stirred further for 2 hours at room temperature. Water (20 ml) was added thereto and the mixture thus obtained was washed with diethyl ether (40 ml). The water layer was filtered and the filtrate thus obtained was adjusted to pH 2.0 with 1N aqueous hydrochloric acid while cooling with ice and stirring and extracted with ethyl acetate (100 ml). The ethyl acetate was washed with 1N aqueous hydrochloric acid (50 ml) and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure and crystallized by cooling with ice to give N-α-naphthalenesulfonyl-L-alanyl-L-proline[yield: 1.77 g, 47.0%).

Workup

  1. additionwas added dropwise to the solution
  2. temperaturewhile cooling with ice
  3. additionAfter the addition
  4. stirringthe mixture was stirred further for 2 hours at room temperature
  5. customthe mixture thus obtained
  6. washwas washed with diethyl ether (40 ml)
  7. filtrationThe water layer was filtered
  8. customthe filtrate thus obtained
  9. temperaturewhile cooling with ice
  10. stirringstirring
  11. extractionextracted with ethyl acetate (100 ml)
  12. washThe ethyl acetate was washed with 1N aqueous hydrochloric acid (50 ml)
  13. dry with materialdried over anhydrous magnesium sulfate
  14. concentrationThe solution was concentrated under reduced pressure
  15. customcrystallized
  16. temperatureby cooling with ice

Sources & evidence

ORD record
ord-3fd39ca6c9bd4f198e393c5bc03265c5
Source dataset
uspto-grants-1990_11
Patent number
US04971993

Reaction notes

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