Ethyl 4-methylpiperidine-2-carboxylate → HCID 178468857, compound

HRID 66315Notes

Reaction equation

HRID 66315 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][NH:5][CH:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:3]1.N#N.Cl.[CH:16]1[C:29]2[S:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[O:21][C:20]=2[CH:19]=[CH:18][C:17]=1[S:30]([NH:33][C@H:34]([C:42](Cl)=[O:43])[CH2:35][CH2:36][CH2:37][NH:38][C:39](=[NH:41])[NH2:40])(=[O:32])=[O:31]>C(Cl)(Cl)Cl>[CH:16]1[C:29]2[S:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[O:21][C:20]=2[CH:19]=[CH:18][C:17]=1[S:30]([NH:33][C@H:34]([C:42]([N:5]1[CH2:6][CH2:7][CH:2]([CH3:1])[CH2:3][CH:4]1[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:43])[CH2:35][CH2:36][CH2:37][NH:38][C:39](=[NH:40])[NH2:41])(=[O:31])=[O:32]

Participants

4

Reactant 2

HCID 15697772Ethyl 4-methylpiperidine-2-carboxylateHCID 178479594HCID 178479594, compound

Product 1

HCID 178468857HCID 178468857, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred solution of 3.6 g of ethyl 4-methyl-2-piperidinecarboxylate in 50 ml of chloroform, which was cooled in an ice-salt bath, was added in portions N2 -(2-phenoxathiinylsulfonyl)-L-arginyl chloride hydrochloride obtained above. The reaction mixture was stirred overnight at room temperature. At the end of this period, 50ml of chloroform was added and the chloroform solution was washed twice with 25 ml of saturated sodium chloride solution, dried over Na2SO4 and evaporated in vacuo. The oily residue was washed with ether to give 3.5 g of powdery ethyl 1-[N2 -(2-phenoxathiinylsulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylate.

Workup

  1. customobtained above
  2. washthe chloroform solution was washed twice with 25 ml of saturated sodium chloride solution
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo
  5. washThe oily residue was washed with ether

Sources & evidence

ORD record
ord-ca41bc85f6744691a8cf5d740e9e44c1
Source dataset
uspto-grants-1978_12
Patent number
US04131673

Reaction notes

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