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

HRID 2106965Notes

Reaction equation

HRID 2106965 reaction equation
[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]

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-fbeeed3d18824d14a975a3773f87247e
Source dataset
uspto-grants-1990_06
Patent number
US04931591

Reaction notes

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