Triethylamine → diphenylmethyl 2-[(4S)-4-phenylacetamido-3-oxo-2-isoxazolidinyl]-5-oxo-2,5-dihydro-2-furancarboxylate

HRID 232212Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 232212
[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.Cl[C:18]1([C:24]([O:26][CH:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH:22]=[CH:21][C:20](=[O:23])[O:19]1.C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[C:1]1([CH2:7][C:8]([NH:10][C@H:11]2[CH2:15][O:14][N:13]([C:18]3([C:24]([O:26][CH:27]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)=[O:25])[CH:22]=[CH:21][C:20](=[O:23])[O:19]3)[C:12]2=[O:16])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 20030875HCID 20030875, VerbindungHCID 56633768(4S)-4-phenylacetamido-3-isoxazolidinone

Produkt 1

HCID 67902310diphenylmethyl 2-[(4S)-4-phenylacetamido-3-oxo-2-isoxazolidinyl]-5-oxo-2,5-dihydro-2-furancarboxylateAusbeute 71,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In 2.5 ml of dichloromethane suspension of 35 mg of (4S)-4-phenylacetamido-3-isoxazolidinone and 50 mg of diphenylmethyl 2-chloro-5-oxo-2,5-dihydro-2-furancarboxylate obtained in Example 49 was added under ice-cooling and stirring, 0.025 ml of triethylamine. The reaction solution was stirred at room temperature for 30 minutes, which was diluted with ethyl acetate, followed by washed with water and drying (Na2SO4). The solvent was evaporated off, and the residue was subjected to a silica gel column chromatography, followed by elution with hexane-ethyl acetate (1:1) to give 56 mg of the subject Compound (51) as colorless crystals. Recryslallization from dichloromethaneethylether afforded colorless prisms, m.p. 168°-169° C. (decomp.).

Aufarbeitung

  1. additionwas added under ice-
  2. temperaturecooling
  3. stirringThe reaction solution was stirred at room temperature for 30 minutes
  4. washby washed with water
  5. dry with materialdrying (Na2SO4)
  6. customThe solvent was evaporated off
  7. washfollowed by elution with hexane-ethyl acetate (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-b1f80655838d4e0d9bc9002039614732
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04851422

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