Water → N-(4-phenylbutanoyl)-L-thioproline

HRID 2073179Notes

Reaction equation

HRID 2073179 reaction equation
[NH:1]1[CH2:8][S:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].O.[C:10]1([CH2:16][CH2:17][CH2:18][C:19](Cl)=[O:20])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>[OH-].[Na+].C1C=CC=CC=1.C(Cl)(Cl)Cl.CO>[C:10]1([CH2:16][CH2:17][CH2:18][C:19]([N:1]2[CH2:8][S:7][CH2:6][C@H:2]2[C:3]([OH:5])=[O:4])=[O:20])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 3

HCID 962WaterHCID 93176L-ThioprolineHCID 117898654-Phenylbutanoyl Chloride

Product 1

HCID 14672237N-(4-phenylbutanoyl)-L-thioprolineYield 81.9%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 14798Sodium HydroxideSolvent2×HCID 21584188Chloroform methanolSolvent

Procedure

6.65 g of L-thioproline was dissolved in 100 ml of 1N sodium hydroxide. After the addition of 50 ml of water to the solution, a solution prepared by dissolving 9.10 g of 4-phenylbutanoyl chloride in 50 ml of benzene was added dropwise with stirring. Subsequently, 50 ml of 1N sodium hydroxide was further added and the mixture was stirred overnight. The benzene layer was removed and the water layer was washed twice with 70 ml of ether. To this water layer was added 7% hydrochloric acid to acidify it, followed by extraction with 70 ml of ethyl acetate three times. The extract was dried over anhydrous sodium sulfate. Ethyl acetate was evaporated to obtain an oily residue, which was subjected to column chromatography on silica gel using chloroform-methanol as an eluent to obtain a fraction of 11.4 g of N-(4-phenylbutanoyl)-L-thioproline as colorless crystals.

Workup

  1. customa solution prepared
  2. additionwas added dropwise
  3. stirringthe mixture was stirred overnight
  4. customThe benzene layer was removed
  5. washthe water layer was washed twice with 70 ml of ether
  6. additionTo this water layer was added 7% hydrochloric acid
  7. extractionfollowed by extraction with 70 ml of ethyl acetate three times
  8. dry with materialThe extract was dried over anhydrous sodium sulfate
  9. customEthyl acetate was evaporated
  10. customto obtain an oily residue, which

Sources & evidence

ORD record
ord-d4bd9e836a3b4324bdcf2b11f1362e6f
Source dataset
uspto-grants-1990_04
Patent number
US04916146

Reaction notes

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