Hydrochloric Acid → (2-Carbamoylethyl)-alpha-naphthoxymalonic acid diethyl ester

HRID 4593

Reaktionsgleichung

Reaktionsgleichung von HRID 4593
[C:1]([CH2:4][CH2:5]C(OC1C2C(=CC=CC=2)C=CC=1)C(O)=O)(=[O:3])[NH2:2].N12CCCN=C1CCCCC2.[CH2:32]([O:34][C:35](=[O:53])[CH:36]([O:42][C:43]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH:46]=[CH:45][CH:44]=1)[C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH3:33].C(N)(=O)C=C.Cl>C(#N)C.O>[CH2:40]([O:39][C:37](=[O:38])[C:36]([CH2:5][CH2:4][C:1](=[O:3])[NH2:2])([O:42][C:43]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH:46]=[CH:45][CH:44]=1)[C:35]([O:34][CH2:32][CH3:33])=[O:53])[CH3:41]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 6579AcrylamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 230496494-Carbamoyl-2(R,S)-alpha-naphthoxybutyric acidHCID 54105534alpha-Naphthoxymalonic acid diethyl ester

Produkt 1

HCID 54384256(2-Carbamoylethyl)-alpha-naphthoxymalonic acid diethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

4-Carbamoyl-2(R,S)-α-naphthoxybutyric acid: 1.49 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene are added to a solution of 3 g of α-naphthoxymalonic acid diethyl ester (Example 36a) and 0.71 g of acrylamide in 5 ml of acetonitrile and the whole is stirred at room temperature for 24 hours. 25 ml of water are added to the reaction mixture, which is adjusted to pH 2 with 2N hydrochloric acid and extracted with ether. The ethereal phases are washed with water and brine, dried over sodium sulphate and concentrated by evaporation, leaving (2-carbamoylethyl)-α-naphthoxymalonic acid diethyl ester.

Aufarbeitung

  1. extractionextracted with ether
  2. washThe ethereal phases are washed with water and brine
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-822d95ff4f2445239bc38f50ab6bd0a8
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04727060

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