Water → HCID 14819290, compound

HRID 2352394Notes

Reaction equation

HRID 2352394 reaction equation
Cl.[C:2]([O:6][C:7](=[O:11])[C@H:8]([CH3:10])[NH2:9])([CH3:5])([CH3:4])[CH3:3].Br[CH:13]1[CH2:18][CH2:17][O:16][C:14]1=[O:15].C(N(CC)CC)C.O>CN(C)C=O>[C:2]([O:6][C:7](=[O:11])[C@H:8]([CH3:10])[NH:9][CH:13]1[CH2:18][CH2:17][O:16][C:14]1=[O:15])([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 954632(3H)-Furanone, 3-bromodihydro-HCID 11275390tert-Butyl alaninate hydrochloride

Product 1

HCID 14819290HCID 14819290, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Dissolved in 30 ml of dimethylformamide were 2.54 g of L-alanine t-butyl ester hydrochloride and 2.38 g of 2-bromo-γ-butyrolactone. After a dropwise addition of 2.83 g of triethylamine, the resultant mixture was heated and stirred at 70° C. for 5 hours. The reaction mixture was poured into chilled water, followed by extraction with ethyl acetate. The extract was washed successivley with water, a 2% aqueous solution of sodium hydrogencarbonate, and water. After drying the extract over anhydrous sodium sulfate, it was distilled under reduced pressure. The residue was isolated and purified by chromatography on a silica gel column (toluene:ethyl acetate=20:1), thereby obtaining 1.86 g of N-(2-oxo-3-tetrahydrofuranyl)-L-alanine t-butyl ester as a colorless oily substance.

Workup

  1. additionThe reaction mixture was poured
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe extract was washed successivley with water
  4. customAfter drying the
  5. extractionextract over anhydrous sodium sulfate, it
  6. distillationwas distilled under reduced pressure
  7. customThe residue was isolated
  8. custompurified by chromatography on a silica gel column (toluene:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-6d129199e49c4f8d8a9caf4f117ea305
Source dataset
uspto-grants-1989_10
Patent number
US04876359

Reaction notes

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