Hydrochloric Acid → HCID 14858836, compound

HRID 1073984Notes

Reaction equation

HRID 1073984 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].[CH2:14]([S:21](Cl)(=[O:23])=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O.Cl>[OH-].[Na+].O1CCOCC1>[CH2:14]([S:21]([NH: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])(=[O:23])=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 74740Phenylmethanesulfonyl chlorideHCID 83525L-Alanyl-L-proline

Product 1

HCID 14858836HCID 14858836, 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 (3 ml), and dioxane (7 ml) solution of benzylsulfonylchloride (1.91 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 using 1N aqueous sodium hydroxide. After completion of the addition, the mixture was further stirred for 2 hours at room temperature. Water (20 ml) was added thereto and the mixture was washed with diethyl ether (40 ml). The water layer was filtered and the filtrate thus obtained was adjusted to pH 1.5 with 1N aqueous hydrochloric acid while cooling with ice and stirring to precipitate N-benzylsulfonyl-L-alanyl-L-proline in a crystalline form[yield: 1.78 g, 52.3%).

Workup

  1. additionwas added dropwise to the solution
  2. temperaturewhile cooling with ice
  3. additionAfter completion of the addition
  4. stirringthe mixture was further stirred for 2 hours at room temperature
  5. washthe mixture was washed with diethyl ether (40 ml)
  6. filtrationThe water layer was filtered
  7. customthe filtrate thus obtained
  8. temperaturewhile cooling with ice
  9. stirringstirring
  10. customto precipitate N-benzylsulfonyl-L-alanyl-L-proline in a crystalline form[yield: 1.78 g, 52.3%)

Sources & evidence

ORD record
ord-e49cd5c66b044547a94cb4ab006eba6b
Source dataset
uspto-grants-1990_11
Patent number
US04971993

Reaction notes

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