Triethylamine → HCID 54377577, compound

HRID 1290074Notes

Reaction equation

HRID 1290074 reaction equation
ClC([O:4][C:5](Cl)(Cl)Cl)=O.C(N(CC)CC)C.[CH2:16]([O:23][C:24](=[O:34])[C@H:25]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[NH2:26])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH3:35][CH:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1>O1CCCC1>[CH2:16]([O:23][C:24](=[O:34])[C@H:25]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[NH:26][C:5]([N:39]1[CH2:40][CH2:41][CH:36]([CH3:35])[CH2:37][CH2:38]1)=[O:4])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 693814-MethylpiperidineHCID 736312Benzyl 3-phenyl-L-alaninate

Product 1

HCID 54377577HCID 54377577, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Trichloromethyl chloroformate (0.44 ml) was added to a solution of triethylamine (1.48 g) in dry tetrahydrofuran (15 ml) under ice-cooling and a solution of L-phenylalanine benzyl ester (1.27 g) in dry tetrahydrofuran (7.5 ml) was dropwise added slowly. Then, a solution of 4-methylpiperidine (1.15 ml) in dry tetrahydrofuran (7.5 ml) was dropwise added. The mixture was stirred at room temperature for 1 hour. The resulting salt was collected by filtration and washed with ethyl acetate (70 ml). The combined filtrate was washed twice with 0.1N hydrochloric acid, twice with a saturated aqueous solution of NaHCO3 and saturated brine, and dried over MgSO4. The solvent was distilled away under reduced pressure. The residue was purified by silica gel column chromatography (eluted with AcOEt/Hex=4/6 v/v) to give 1.86 g of the title compound as a colorless oil (see Table 11).

Workup

  1. temperaturecooling
  2. filtrationThe resulting salt was collected by filtration
  3. washwashed with ethyl acetate (70 ml)
  4. washThe combined filtrate was washed twice with 0.1N hydrochloric acid, twice with a saturated aqueous solution of NaHCO3 and saturated brine
  5. dry with materialdried over MgSO4
  6. distillationThe solvent was distilled away under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluted with AcOEt/Hex=4/6 v/v)

Sources & evidence

ORD record
ord-f60504a4205b4fcba8a9c745a3b70715
Source dataset
uspto-grants-1998_05
Patent number
US05750696

Reaction notes

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