Water → N-(4-oxo-1-adamantyl)acetamide

HRID 1680602

Reaktionsgleichung

Reaktionsgleichung von HRID 1680602
Br[C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([C:5]3=[O:12])[CH2:3]1)[CH2:9]2.[OH2:13].[C:14](#[N:16])[CH3:15]>>[O:12]=[C:5]1[CH:6]2[CH2:7][CH:8]3[CH2:9][C:2]([NH:16][C:14](=[O:13])[CH3:15])([CH2:3][CH:4]1[CH2:10]3)[CH2:11]2

Komponenten

4

Edukt 3

HCID 962WaterHCID 6342Acetonitrile2×HCID 5909055-Bromo-2-adamantanone

Produkt 1

HCID 5338964N-(4-oxo-1-adamantyl)acetamide

Versuchsvorschrift

A solution of 1.2 g of nitryltetrafluoroborate in 15 ml of acetonitrile is cooled to 0° C. and a solution of 2.17 g of 5-bromo-2-oxoadamantane [preparation is described in H. W. Geluk, SYNTHESIS, p. 374 (1972)] in 15 ml of acetonitrile is added with rapid stirring and cooling. The reaction mixture is stirred for 30 minutes then poured into water and extracted with diethyl ether. The diethyl ether extract is washed with 5% sodium bicarbonate solution and water and dried over magnesium sulfate. The solvent is removed under reduced pressure to give N-(2-oxoadamantan-5-yl)acetamide. Substitution of an equivalent quantity of N-(2-oxoadamantan-5-yl)acetamide for the methyl 2-oxoadamantane-1-carbamate of Example 57 and substantial repetition of the procedures detailed therein provides methyl L-tyrosyl-D-methionylglycyl-L-phenylalanyl-5-amino-2-adamantanecarboxylate hydrochloride which is represented by the formula ##STR68##

Aufarbeitung

  1. temperaturecooling
  2. stirringThe reaction mixture is stirred for 30 minutes
  3. extractionextracted with diethyl ether
  4. extractionThe diethyl ether extract
  5. washis washed with 5% sodium bicarbonate solution and water
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent is removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-077048258e9040c3b446ee6f9593780c
Quelldatensatz
uspto-grants-1981_06
Patentnummer
US04273704

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