Ethanol → Ethyl 3-(3-cyclohexyl-3-hydroxypropyl)-2,5-dioxo-4-imidazolidineheptanoate

HRID 444051Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 444051
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[N:14]([CH2:15][CH2:16][CH:17]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[OH:18])[C:13](=[O:25])[NH:12][C:11]1=[O:26])([OH:3])=[O:2].[CH2:27](O)[CH3:28]>S(=O)(=O)(O)O>[CH2:27]([O:2][C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[N:14]([CH2:15][CH2:16][CH:17]([CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[OH:18])[C:13](=[O:25])[NH:12][C:11]1=[O:26])=[O:3])[CH3:28]

Komponenten

4

Edukt 2

HCID 702EthanolHCID 1193043-(3-Cyclohexyl-3-hydroxypropyl)-2,5-dioxo-4-imidazolidineheptanoic acid

Produkt 1

HCID 12788653Ethyl 3-(3-cyclohexyl-3-hydroxypropyl)-2,5-dioxo-4-imidazolidineheptanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

A solution of 5-(6-carboxyhexyl)-1-(3-cyclohexyl-3-hydroxypropyl)hydantoin (diastereomer of m.p. 96°-98°) (Example 14c) (4 g) in ethanol (60 ml) and concentrated sulphuric acid (1.6 ml) was allowed to stand at room temperature for 18 hours. The alcohol was evaporated, water was added, and the precipitated oil was extracted with ether. The ether solution was washed with sodium bicarbonate solution and with water, dried (MgSO4) and evaporated to give a single diastereomer of 5-(6-ethoxycarbonylhexyl)-1-(3-cyclohexyl-3-hydroxypropyl)hydantoin as a colourless oil, soon solidifying, and crystallising from cyclohexane in small colourless plates, m.p. 62°-63°.

Aufarbeitung

  1. customThe alcohol was evaporated
  2. additionwater was added
  3. extractionthe precipitated oil was extracted with ether
  4. washThe ether solution was washed with sodium bicarbonate solution and with water
  5. dry with materialdried (MgSO4)
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-aabcae5ebaad4079ab40c8dc76385edb
Quelldatensatz
uspto-grants-1981_04
Patentnummer
US04262128

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