Triethylamine → HCID 178501369, compound

HRID 2249977Notes

Reaction equation

HRID 2249977 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:14])[C@@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].C(N(CC)CC)C.[CH:22]([C@H:25]1[CH2:30][CH2:29][C@H:28]([C:31](O)=[O:32])[CH2:27][CH2:26]1)([CH3:24])[CH3:23]>ClC(Cl)C>[CH3:2][O:3][C:4](=[O:14])[C@@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH:6][C:31]([C@H:28]1[CH2:29][CH2:30][C@H:25]([CH:22]([CH3:24])[CH3:23])[CH2:26][CH2:27]1)=[O:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11481330methyl (2R)-2-amino-3-phenylpropanoate;hydrochlorideHCID 178448099HCID 178448099, compound

Product 1

HCID 178501369HCID 178501369, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

D-Phenylalanine methyl ester hydrochloride (20 g, 0.092 mol) was suspended in a solution of triethylamine (66 mL) in dichloroethane (100 mL) and the mixture was stirred for 1 hour at room temperature. The organic layer was separated after washing with water and dried over anhydrous sodium sulphate. Trans-4-isopropylcyclohexane carboxylic acid (15.8 g, 0.092 mol) was added to the organic layer followed by LiOH—Al2O3 (5.5 g of LiOH adsorbed on 40.5 g aluminum oxide) and the resulting mixture heated at for 24 hours. The reaction mixture was filtered through a celite bed and washed with 1.5 N HCl, 5% sodium bicarbonate solution and brine. The organic layer was concentrated to yield 15.5 g of N-(trans-4-isopropylcyclohexylcarbonyl)-D-phenylalanine methyl ester.

Workup

  1. customThe organic layer was separated
  2. washafter washing with water
  3. dry with materialdried over anhydrous sodium sulphate
  4. temperaturethe resulting mixture heated at for 24 hours
  5. filtrationThe reaction mixture was filtered through a celite bed
  6. washwashed with 1.5 N HCl, 5% sodium bicarbonate solution and brine
  7. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-7fe3a0a784d44bc984df5bd0abdf3b36
Source dataset
uspto-grants-2008_01
Patent number
US07314955B2

Reaction notes

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