HOAc dioxane → (S)-2-[[(S)-2-(Acetoxyacetyl)-1-pyrrolidinyl]carbonyl]-N-(phenylmethyl)-1-pyrrolidinecarboxamide

HRID 1735395

Reaktionsgleichung

Reaktionsgleichung von HRID 1735395
[N+](=[CH:3][C:4]([C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11]([C@@H:13]1[CH2:17][CH2:16][CH2:15][N:14]1[C:18]([NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])=[O:12])=[O:5])=[N-].[C:28]([OH:31])(=[O:30])[CH3:29].O1CCOCC1>>[C:28]([O:31][CH2:3][C:4]([C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11]([C@@H:13]1[CH2:17][CH2:16][CH2:15][N:14]1[C:18]([NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])=[O:12])=[O:5])(=[O:30])[CH3:29]

Komponenten

3

Edukt 2

HCID 22565020HOAc dioxaneHCID 54423239(S)-2-[[(S)-2-(Diazoacetyl)-1-pyrrolidinyl]carbonyl]-N-(phenylmethyl)-1-pyrrolidinecarboxamide

Produkt 1

HCID 15389023(S)-2-[[(S)-2-(Acetoxyacetyl)-1-pyrrolidinyl]carbonyl]-N-(phenylmethyl)-1-pyrrolidinecarboxamide

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

(S)-2-[[(S)-2-(Diazoacetyl)-1-pyrrolidinyl]carbonyl]-N-(phenylmethyl)-1-pyrrolidinecarboxamide (3.63 g) was dissolved in acetic acid-1,4-dioxane (1:1, 36 ml), and the mixture was heated at 100° C. for 10 minutes. The reaction mixture was concentrated, added with methylene chloride, washed with a saturated aqueous solution of sodium bicarbonate and water in order, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (eluent: chloroform-methanol) to give the title compound (1.47 g) (see Table 1).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. additionadded with methylene chloride
  3. washwashed with a saturated aqueous solution of sodium bicarbonate and water in order
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (eluent: chloroform-methanol)

Quellen und Nachweise

ORD-Eintrag
ord-22e1f570dc3c4e3b92ba19b42c1e9362
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05536737

Verknüpfte Notizen

Wird geladen…