Triethylamine → HCID 67901865, compound

HRID 232204Notes

Reaction equation

HRID 232204 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[CH2:15][O:14][NH:13][C:12]2=[O:16])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl[C:25]1([C:31]([O:33][CH3:34])=[O:32])[CH:29]=[CH:28][C:27](=[O:30])[O:26]1>ClCCl>[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[CH2:15][O:14][N:13]([C:25]3([C:31]([O:33][CH3:34])=[O:32])[CH:29]=[CH:28][C:27](=[O:30])[O:26]3)[C:12]2=[O:16])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20030931Methyl 2-chloro-2,5-dihydro-5-oxo-2-furancarboxylateHCID 54136951HCID 54136951, compound

Product 1

HCID 67901865HCID 67901865, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 8 ml of dichloromethane was suspended 110 mg of (4R)-4-phenylacetamido-3-isoxazolidinone. To the suspension were added, under ice-cooling and stirring, 0.14 ml of triethylamine and 2 ml of dichloromethane solution dissolving 106 mg of the Compound (27) obtained in Example (27). The reaction solution was stirred at room temperature for 40 minutes, washed with water and dried (Na2SO4). The solvent was then evaporated off. The residue was subjected to a silica gel column chromatography, followed by elution with hexane-ethyl acetate (2:3) to give 78 mg of the subject Compound (30) as colorless oil.

Workup

  1. additionTo the suspension were added, under ice-
  2. temperaturecooling
  3. stirringThe reaction solution was stirred at room temperature for 40 minutes
  4. washwashed with water
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was then evaporated off
  7. washfollowed by elution with hexane-ethyl acetate (2:3)

Sources & evidence

ORD record
ord-1197f54c5b33431e9222ee5e31af62c3
Source dataset
uspto-grants-1989_07
Patent number
US04851422

Reaction notes

Loading…