Triethylamine → HCID 178468883, compound

HRID 866892Notes

Reaction equation

HRID 866892 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.[CH3:21][O:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[CH:29]=[C:28]([S:33]([NH:36][C@H:37]([C:45](Cl)=[O:46])[CH2:38][CH2:39][CH2:40][NH:41][C:42](=[NH:44])[NH2:43])(=[O:35])=[O:34])[CH:27]=[CH:26]2>C(Cl)(Cl)Cl>[CH3:21][O:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[CH:29]=[C:28]([S:33]([NH:36][C@H:37]([C:45]([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:46])[CH2:38][CH2:39][CH2:40][NH:41][C:42](=[NH:43])[NH2:44])(=[O:35])=[O:34])[CH:27]=[CH:26]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27517Ethyl piperidine-2-carboxylateHCID 178487596HCID 178487596, compound

Product 1

HCID 178468883HCID 178468883, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred solution of 2.2 g of ethyl 2-piperidine-carboxylate 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 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 ethyl ether to give 2.9 g of powdery ethyl 1-[N2 -(6-methoxy-2-naphthylsulfonyl)-L-arginyl]-2-piperidinecarboxylate. For analysis of the product, a portion of the product was converted to the flavianate, M.P. 192°-193° C. I.R. (KBr): 3,210, 1,747, 1,638 cm-1

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 ethyl ether

Sources & evidence

ORD record
ord-7b449973f1fc4d5ab2cf47b8d076ba3b
Source dataset
uspto-grants-1978_07
Patent number
US04101653

Reaction notes

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