HCID 178476465, compound → HCID 178492897, compound

HRID 66313Notes

Reaction equation

HRID 66313 reaction equation
C(O)(=O)C.[CH:5]1([C:11]2[CH:12]=[C:13]([S:19]([NH:22][C@H:23]([C:31]([N:33]3[CH2:38][CH2:37][CH:36]([CH3:39])[CH2:35][CH:34]3[C:40]([O:42]CC)=[O:41])=[O:32])[CH2:24][CH2:25][CH2:26][NH:27][C:28](=[NH:30])[NH2:29])(=[O:21])=[O:20])[CH:14]=[CH:15][C:16]=2[O:17][CH3:18])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1>C(O)C.C(Cl)(Cl)Cl>[CH:5]1([C:11]2[CH:12]=[C:13]([S:19]([NH:22][C@H:23]([C:31]([N:33]3[CH2:38][CH2:37][CH:36]([CH3:39])[CH2:35][CH:34]3[C:40]([OH:42])=[O:41])=[O:32])[CH2:24][CH2:25][CH2:26][NH:27][C:28](=[NH:29])[NH2:30])(=[O:20])=[O:21])[CH:14]=[CH:15][C:16]=2[O:17][CH3:18])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

4

Reactant 1

HCID 178476465HCID 178476465, compound

Product 1

HCID 178492897HCID 178492897, compoundYield 73.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

A solution of 2.4 g of ethyl 1-[N2 -(3-cyclohexyl-4-methoxyphenylsulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylate acetate in 10 ml of ethanol and 10 ml of N-NaOH solution was stirred overnight at room temperature. Then, the reaction mixture was concentrated and dissolved in 10 ml of water. The solution was neutralized with 2N-HCl solution to give a white gummy precipitate which was dissolved in 150 ml of chloroform. The chloroform solution was washed with saturated NaCl solution, dried over anhydrous sodium sulfate and evaporated in vacuo to give 1.52 g of 1-[N2 -(3-cyclohexyl-4-methoxyphenylsulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid as an amorphous solid. I.R. (KBr): 3350, 2920, 1620, 1250 cm-1.

Workup

  1. concentrationThen, the reaction mixture was concentrated
  2. dissolutiondissolved in 10 ml of water
  3. customto give a white gummy precipitate which
  4. washThe chloroform solution was washed with saturated NaCl solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-386fe19412ab46d38012debc49ea6699
Source dataset
uspto-grants-1978_12
Patent number
US04131673

Reaction notes

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