Triethylamine → HCID 178468883, compound

HRID 616210Notes

Reaction equation

HRID 616210 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[C:7]([O:9][CH2:10][CH3:11])=[O:8].C(N(CC)CC)C.N#N.Cl.[CH3:22][O:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[CH:30]=[C:29]([S:34]([NH:37][C@H:38]([C:46](Cl)=[O:47])[CH2:39][CH2:40][CH2:41][NH:42][C:43](=[NH:45])[NH2:44])(=[O:36])=[O:35])[CH:28]=[CH:27]2>C(Cl)(Cl)Cl>[CH3:22][O:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[CH:30]=[C:29]([S:34]([NH:37][C@H:38]([C:46]([N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:47])[CH2:39][CH2:40][CH2:41][NH:42][C:43](=[NH:44])[NH2:45])(=[O:36])=[O:35])[CH:28]=[CH:27]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27517Ethyl piperidine-2-carboxylateHCID 178487595HCID 178487595, compound

Product 1

HCID 178468883HCID 178468883, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred solution of 2.2 of ethyl 2-piperidinecarboxylate and 4.1 ml of triethylamine in 50 ml of chloroform, which was cooled in an ice-salt bath, was added in portions N2 -(6-methoxy-2-naphthylsulfonyl)-L-arginyl chloride hydrochloride obtained above. The reaction mixture was stirred overnight at room temperature. At the end of this period, 500 ml of chloroform was added and the chloroform solution was washed twice with 50 ml of saturated sodium chloride solution, dried over anhydrous sodium sulfate and evaporated in vacuo. The oily residue was washed with ether to give 2.9 g of powdery ethyl 1-[N2 -(6-methoxy-2-naphthylsulfonyl)-L-arginyl]-2piperidinecarboxylate. For analysis of the product, a portion of the product was converted to the flavianate, M.P. 192°-3° C.

Workup

  1. customobtained above
  2. washthe chloroform solution was washed twice with 50 ml of saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated in vacuo
  5. washThe oily residue was washed with ether

Sources & evidence

ORD record
ord-399b8ac71b7f4902b4a90d35579be9dc
Source dataset
uspto-grants-1978_02
Patent number
US04072757

Reaction notes

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