Triethylamine → 7-[2-(2-Methoxyphenyl)-2-oxoethylcarbamoyl]heptanoic acid methyl ester

HRID 1616548Notes

Reaction equation

HRID 1616548 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][CH2:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20])=[O:12].[CH3:21][O:22][C:23](=[O:33])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30](O)=[O:31].CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.C(OCC)(=O)C>[CH3:21][O:22][C:23](=[O:33])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30](=[O:31])[NH:9][CH2:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20])=[O:12]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 5541918-Methoxy-8-oxooctanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 222815712-Amino-1-(2-methoxyphenyl)ethan-1-one hydrochloride

Product 1

HCID 684879257-[2-(2-Methoxyphenyl)-2-oxoethylcarbamoyl]heptanoic acid methyl esterYield 88.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add triethylamine (8.1 g, 79.9 mmol) dropwise to a solution of 2-amino-1-(2-methoxyphenyl)ethanone hydrochloride (13.6 g, 67.4 mmol) and octanedioic acid monomethyl ester (14.0 g, 74.2 mmol) in methylene chloride (600 mL) at 0° C. under nitrogen, and then add EDC HCl (15.5 g, 81.0 mmol). Stir the mixture for 4 hours and warm to room temperature with stirring for an additional 18 hours. Dilute the mixture in ethyl acetate (1.2 L), wash sequentially with water (300 mL), 1 N HCl (300 mL), brine (300 mL), saturated sodium, bicarbonate solution (300 mL) and brine (300 mL), and dry over sodium sulfate. Remove the solvent under reduced pressure to afford 7-[2-(2-methoxyphenyl)-2-oxoethylcarbamoyl]heptanoic acid methyl ester (20.0 g, 88%), which is used in the next step without further purification.

Workup

  1. stirringwith stirring for an additional 18 hours
  2. washwash sequentially with water (300 mL), 1 N HCl (300 mL), brine (300 mL), saturated sodium, bicarbonate solution (300 mL) and brine (300 mL)
  3. dry with materialdry over sodium sulfate
  4. customRemove the solvent under reduced pressure

Sources & evidence

ORD record
ord-51e9c8a3b5c94e508399fe339980e2ba
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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