Triethylamine → Ethyl 2-[[3-[[[4-(2-pyridyloxy)phenyl]carbonylamino]methyl]-4-methoxyphenyl]methyl]butyrate

HRID 347670Notes

Reaction equation

HRID 347670 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:5]=[C:6]([CH2:12][CH:13]([CH2:19][CH3:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11].C(N(CC)CC)C.C(Cl)(=O)OCC.[N:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[O:40][C:41]1[CH:49]=[CH:48][C:44]([C:45](O)=[O:46])=[CH:43][CH:42]=1>C(Cl)Cl>[N:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[O:40][C:41]1[CH:49]=[CH:48][C:44]([C:45]([NH:2][CH2:3][C:4]2[CH:5]=[C:6]([CH2:12][CH:13]([CH2:19][CH3:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:7]=[CH:8][C:9]=2[O:10][CH3:11])=[O:46])=[CH:43][CH:42]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 22139981Ethyl 2-[(3-aminomethyl-4-methoxyphenyl)-methyl]butyrate hydrochlorideHCID 222620524-(Pyridin-2-yloxy)benzoic acid

Product 1

HCID 21083633Ethyl 2-[[3-[[[4-(2-pyridyloxy)phenyl]carbonylamino]methyl]-4-methoxyphenyl]methyl]butyrateYield 68.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl 2-[(3-aminomethyl-4-methoxyphenyl)-methyl]butyrate hydrochloride (302 mg, 1.00 mmol) [Japanese Patent Application No. 2000-158424] and triethylamine (390 μL, 2.80 mmol) in 10 mL of dehydrated methylene chloride was added ethyl chlorocarbonate (105 μL, 1.10 mmol) under cooling with ice and stirring, and the mixture was stirred for 20 minutes under cooling with ice. Next, 4-(2-pyridyloxy)benzoic acid (237 mg, 1.10 mmol) was added and the mixture was stirred for 1 hour under cooling with ice and for 5 hours at room temperature. Methylene chloride was added to the reaction mixture, which was washed with water, brine, then dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=3:2 v/v) to obtain 317 mg (68%) of the title compound as a colorless oil.

Workup

  1. temperatureunder cooling with ice
  2. stirringthe mixture was stirred for 20 minutes
  3. temperatureunder cooling with ice
  4. stirringthe mixture was stirred for 1 hour
  5. washwas washed with water, brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=3:2 v/v)

Sources & evidence

ORD record
ord-47b218c968d140058d444b0cec84a3e7
Source dataset
uspto-grants-2007_02
Patent number
US07176204B2

Reaction notes

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