Sodium Hydroxide → HCID 178487597, compound

HRID 1833568Notes

Reaction equation

HRID 1833568 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([NH:16][C@H:17]([C:25]([N:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH:28]1[C:33]([O:35]CC)=[O:34])=[O:26])[CH2:18][CH2:19][CH2:20][NH:21][C:22](=[NH:24])[NH2:23])(=[O:15])=[O:14])[CH:7]=[CH:6]2.[OH-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([NH:16][C@H:17]([C:25]([N:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH:28]1[C:33]([OH:35])=[O:34])=[O:26])[CH2:18][CH2:19][CH2:20][NH:21][C:22](=[NH:23])[NH2:24])(=[O:14])=[O:15])[CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178468883HCID 178468883, compound

Product 1

HCID 178487597HCID 178487597, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.8 g of ethyl 1-[N2 -(6-methoxy-2-naphthylsulfonyl)-L-arginyl]-2-piperidinecarboxylate in 15 ml of methanol and 10 ml of 2N-NaOH solution was warmed to 60° C and held at that temperature for 10 hours. At the end of this period, the reaction mixture was concentrated and chromatographed on 200 ml of Daiaion® SK 102 ion exchange resin (200 -- 300 mesh, H30 form, manufactured by Mitsubishi Chemical Industries Limited) packed in water, washed with ethanol-water (1:4) and eluted with ethanol-water-NH4OH (10:9:1). The main fraction was evaporated to dryness and washed with ethyl ether to give 2.0 g of 1-[N2 -(6-methoxy-2-naphthylsulfonyl)-L-arginyl]-2-piperidinecarboxylic acid as an amorphous solid. I.R. (KBr): 3,200 (broad), 1,620, 1,150 cm-1

Workup

  1. concentrationAt the end of this period, the reaction mixture was concentrated
  2. customchromatographed on 200 ml of Daiaion® SK 102 ion exchange resin (200 -- 300 mesh, H30 form, manufactured by Mitsubishi Chemical Industries Limited)
  3. washwashed with ethanol-water (1:4)
  4. washeluted with ethanol-water-NH4OH (10:9:1)
  5. customThe main fraction was evaporated to dryness
  6. washwashed with ethyl ether

Sources & evidence

ORD record
ord-01b8bb68f06e4790af1b78f79868f59d
Source dataset
uspto-grants-1978_01
Patent number
US04066773

Reaction notes

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