Hydrochloric Acid → Ethyl 2-amino-4-[8-(2-methoxyethoxy)naphthalen-2-ylmethyl]-5-methylhexanoate

HRID 252410Notes

Reaction equation

HRID 252410 reaction equation
C([O:3][C:4]1[CH:5]([CH2:13][CH:14]([CH2:18][C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[C:22]([O:29][CH2:30][CH2:31][O:32][CH3:33])[CH:23]=[CH:24][CH:25]=3)[CH:20]=2)[CH:15]([CH3:17])[CH3:16])[N:6]=C(OCC)CN=1)C.Cl.[C:35](=[O:38])(O)[O-].[Na+].[C:40](#N)C>>[NH2:6][CH:5]([CH2:13][CH:14]([CH2:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[C:22]([O:29][CH2:30][CH2:31][O:32][CH3:33])[CH:23]=[CH:24][CH:25]=2)[CH:20]=1)[CH:15]([CH3:16])[CH3:17])[C:4]([O:38][CH2:35][CH3:40])=[O:3]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 668877873,6-Diethoxy-2-{2-[8-(2-methoxyethoxy)naphthalen-2-ylmethyl]-3-methylbutyl}-2,5-dihydropyrazine

Product 1

HCID 66888631Ethyl 2-amino-4-[8-(2-methoxyethoxy)naphthalen-2-ylmethyl]-5-methylhexanoate

Procedure

A solution of 1.57 g of 3,6-diethoxy-2-{2-[8-(2-methoxyethoxy)naphthalen-2-ylmethyl]-3-methylbutyl}-2,5-dihydropyrazine in 14 ml of acetonitrile at room temperature is admixed with 14 ml of 1N HCl. After 30 minutes, the reaction mixture is poured into a stirred mixture of 15 ml of saturated aqueous sodium bicarbonate solution and 15 g of ice, and the mixture is extracted with dichloromethane (3×). The combined organic phases are washed with water (3×), dried with sodium sulphate and concentrated by evaporation. The crude title compound is identified on the basis of the Rf value from the residue.

Workup

  1. customat room temperature
  2. extractionthe mixture is extracted with dichloromethane (3×)
  3. washThe combined organic phases are washed with water (3×)
  4. dry with materialdried with sodium sulphate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-6ae3986d87b048deaca3f47422b6b17b
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

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