Hexane → HCID 13985872, compound

HRID 2073180Notes

Reaction equation

HRID 2073180 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@@H:2]1[C:3]([OH:5])=[O:4].[C:9]1([CH2:15][CH2:16][CH2:17][C:18](Cl)=[O:19])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CCCCCC>[OH-].[Na+].O.C1C=CC=CC=1>[C:9]1([CH2:15][CH2:16][CH2:17][C:18]([N:1]2[CH2:8][CH2:7][CH2:6][C@@H:2]2[C:3]([OH:5])=[O:4])=[O:19])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 3

HCID 8058HexaneHCID 8988D-ProlineHCID 117898654-Phenylbutanoyl Chloride

Product 1

HCID 13985872HCID 13985872, compoundYield 67.4%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

3.45 g of D-proline was dissolved in 60 ml of 1N of sodium hydroxide and 30 ml of water. To the solution thus obtained, a solution prepared by dissolving 5.56 g of 4-phenylbutanoyl chloride in 30 ml of benzene was added dropwise with stirring. Subsequently, 30 ml of 1N sodium hydroxide was further added and the mixture was stirred at room temperature overnight. The benzene layer was removed and the water layer was washed twice with 50 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 treated with hexane to obtain 5.28 g of N-(4-phenylbutanoyl)-D-proline as colorless crystals.

Workup

  1. customTo the solution thus obtained
  2. customa solution prepared
  3. additionwas added dropwise
  4. stirringthe mixture was stirred at room temperature overnight
  5. customThe benzene layer was removed
  6. washthe water layer was washed twice with 50 ml of ether
  7. additionTo this water layer was added 7% hydrochloric acid
  8. extractionfollowed by extraction with 70 ml of ethyl acetate three times
  9. dry with materialThe extract was dried over anhydrous sodium sulfate
  10. customEthyl acetate was evaporated
  11. customto obtain an oily residue, which

Sources & evidence

ORD record
ord-4b41f33d839f44ac9e8da282a5f5ba6d
Source dataset
uspto-grants-1990_04
Patent number
US04916146

Reaction notes

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