Hydrochloric Acid → (2S)-2-[(4-morpholinylsulfonyl)amino]-3-phenylpropanoic acid

HRID 727777Notes

Reaction equation

HRID 727777 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][C@H:8]([NH2:12])[C:9]([OH:11])=[O:10])=[CH:3][CH:2]=1.[OH-].[Na+].N1([NH:21][S:22](Cl)(=[O:24])=[O:23])CCOCC1.Cl.[CH2:27]1[CH2:31][O:30][CH2:29][CH2:28]1>O>[N:21]1([S:22]([NH:12][C@H:8]([C:9]([OH:11])=[O:10])[CH2:7][C:4]2[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=2)(=[O:24])=[O:23])[CH2:27][CH2:31][O:30][CH2:29][CH2:28]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6140L-PhenylalanineHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 13271200Morpholin-4-ylsulfamyl chloride

Product 1

HCID 10859978(2S)-2-[(4-morpholinylsulfonyl)amino]-3-phenylpropanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of L-PHE (66 g), NaOH (16 g), and water (120 mL) was treated dropwise with a solution of 4-morpholinylsulfamyl chloride (37 g, prepared according to the methods of R. Wegler and K. Bodenbenner, Anallen der Chemie, 624, 25 (1959) and G. Weiss and G. Schulze, Anallen der Chemie, 729, 40 (1969)) in THF (80 mL). The reaction was stirred for 6 hours at room temperature then concentrated aqueous HCl was added dropwise to bring the solution to pH 2. Product was extracted into EtOAc and this solution was washed with lN HCl, dried over MgSO4 and evaporated. The residue was triturated with ether to give a solid that was recrystallized from water to give morpholinylsulfonyl-PHE. MP 157°-158° C. MS (FAB) 337 (m +Na), 315 (m +1).

Workup

  1. customprepared
  2. extractionProduct was extracted into EtOAc
  3. washthis solution was washed with lN HCl
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residue was triturated with ether
  7. customto give a solid
  8. customthat was recrystallized from water
  9. customto give morpholinylsulfonyl-PHE

Sources & evidence

ORD record
ord-f2a2e4bd0d7141fcbf92f76cf24b7216
Source dataset
uspto-grants-1991_09
Patent number
US05045540

Reaction notes

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