Hydrochloric Acid → HCID 54120551, compound

HRID 1440400Notes

Reaction equation

HRID 1440400 reaction equation
C([O:3][C:4]([CH:6]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:7]([NH:9][C@H:10]([CH2:21][OH:22])[CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)=[O:8])=[O:5])C.CO.[OH-].[K+].Cl>C1COCC1.O>[C:4]([CH:6]([CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:7]([NH:9][C@H:10]([CH2:21][OH:22])[CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)=[O:8])([OH:5])=[O:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 53922769HCID 53922769, compound

Product 1

HCID 54120551HCID 54120551, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cooled and stirred solution of N-(2-ethoxycarbonyl-3-phenylpropionyl)-(L)-tryptophanol (15 g) in THF (40 ml)-methanol (30 ml) was added dropwise a solution of KOH (2.5 g) in water (10 ml). After stirring at 4° C.--room temperature for 20 hours, the reaction mixture was acidified with 1N HCl, diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with brine and dried (MgSO4). The organic solvent was evaporated off to yield N-(2-carboxy-3-phenylpropionyl)-(L)-tryptophanol (13.5 g, 97%) as crystals. Recrystallization from ethyl acetate-hexane gave pale yellow crystals having melting point of 130° to 131° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customThe organic solvent was evaporated off

Sources & evidence

ORD record
ord-bddfc939961b4758856d2d40a088bc86
Source dataset
uspto-grants-1996_03
Patent number
US05498728

Reaction notes

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