Triethylamine → HCID 54006815, compound

HRID 1756774Notes

Reaction equation

HRID 1756774 reaction equation
[CH2:1]1[O:9][C:8]2[C:3](=[C:4]([C@H:10]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:11][C:12]([OH:14])=O)[CH:5]=[CH:6][CH:7]=2)[O:2]1.C(N(CC)CC)C.ClC(OCC)=O.[CH:33]([C:36]1[CH:43]=[CH:42][CH:41]=[C:40]([CH:44]([CH3:46])[CH3:45])[C:37]=1[CH2:38][NH2:39])([CH3:35])[CH3:34]>C1COCC1.C(OCC)(=O)C.O>[CH:44]([C:40]1[CH:41]=[CH:42][CH:43]=[C:36]([CH:33]([CH3:35])[CH3:34])[C:37]=1[CH2:38][NH:39][C:12](=[O:14])[CH2:11][C@H:10]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[O:9][CH2:1][O:2][C:3]=12)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])([CH3:46])[CH3:45]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 22379473HCID 22379473, compoundHCID 54473865HCID 54473865, compound

Product 1

HCID 54006815HCID 54006815, compoundYield 57.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 407 mg (1.54 mmol) of (R)-3-(2, 3-methylenedioxyphenyl) octanoic acid in 8 ml of THF were added 0.24 ml of triethylamine and then 0.15 ml (1.6 mmol) of ethyl chloroformate. After stirring for 20 minutes, a solution of 264 mg (1.38 mmol) of 2, 6-diisopropylbenzylamine in tetrahydrofuran was added to the mixture, which was stirred at room temperature for 2 hours. The reaction mixture was mixed with 10 ml of water and shaken with ethyl acetate. The extract was washed with saturated saline, dried over anhydrous magnesium sulfate and the solvent evaporated in vacuo. The residue was recrystallized from a mixed solvent of hexane and ethyl acetate to give 348 mg of (R)-N-(2, 6-diisopropylbenzyl)-3-(2,3-methylenedioxyphenyl) octanamide as white crystals. Yield, 52%.

Workup

  1. stirringwas stirred at room temperature for 2 hours
  2. washThe extract was washed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent evaporated in vacuo
  5. customThe residue was recrystallized from a mixed solvent of hexane and ethyl acetate

Sources & evidence

ORD record
ord-3f4546c216254a79884950c4951097b2
Source dataset
uspto-grants-1995_08
Patent number
US05442060

Reaction notes

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