Triethylamine → HCID 69551777, compound

HRID 1833268Notes

Reaction equation

HRID 1833268 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:10][C:11](O)=[O:12])[CH:6]=[C:7]([CH3:9])[CH:8]=1.[CH2:14]([O:16][C:17](=[O:31])[CH:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=1)[CH2:19][NH2:20])[CH3:15].C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.C(OCC)(=O)C>[CH2:14]([O:16][C:17](=[O:31])[CH:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=1)[CH2:19][NH:20][C:11](=[O:12])[CH2:10][C:5]1[CH:6]=[C:7]([CH3:9])[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:15]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 39879Acetic acid, 5-methoxy-m-tolyl-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12814098Ethyl 3-amino-2-(3,4-dimethoxyphenyl)propanoate

Product 1

HCID 69551777HCID 69551777, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (3-methoxy-5-methyl-phenyl)-acetic acid (512.8 mg, 2.84 mmol), 3-amino-2-(3,4-dimethoxy-phenyl)-propionic acid ethyl ester (825 mg, 2.84 mmol), and triethylamine (912 uL, 6.54 mmol) in dry methylene chloride (25 mL) was chilled in an ice bath under argon. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (573 mg, 2.98 mmol) was added in one portion and the mixture stirred at room temperature for 72 hrs. The reaction mixture was poured into ethyl acetate (100 mL) and extracted with 2.5% aqueous potassium bisulfate (3×20 mL), 5% aqueous sodium bicarbonate (3×20 mL), and saturated aqueous sodium chloride (20 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo to afford 2-(3,4-dimethoxy-phenyl)-3-[2-(3-methoxy-5-methyl-phenyl)-acetylamino]-propionic acid ethyl ester as a light tan foam (0.79 g, 67%). This material was used without further purification: 1H NMR (300 MHz) compatible.

Workup

  1. extractionextracted with 2.5% aqueous potassium bisulfate (3×20 mL), 5% aqueous sodium bicarbonate (3×20 mL), and saturated aqueous sodium chloride (20 mL)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0f99eb22943b4c5d9e6ce7bd186ecc66
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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