Sodium Hydroxide → HCID 178428661, compound

HRID 66316Notes

Reaction equation

HRID 66316 reaction equation
[CH:1]1[C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[S:15]([NH:18][C@H:19]([C:27]([N:29]1[CH2:34][CH2:33][CH:32]([CH3:35])[CH2:31][CH:30]1[C:36]([O:38]CC)=[O:37])=[O:28])[CH2:20][CH2:21][CH2:22][NH:23][C:24](=[NH:26])[NH2:25])(=[O:17])=[O:16].[OH-].[Na+]>CO>[CH:1]1[C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[S:15]([NH:18][C@H:19]([C:27]([N:29]1[CH2:34][CH2:33][CH:32]([CH3:35])[CH2:31][CH:30]1[C:36]([OH:38])=[O:37])=[O:28])[CH2:20][CH2:21][CH2:22][NH:23][C:24](=[NH:25])[NH2:26])(=[O:16])=[O:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178468857HCID 178468857, compound

Product 1

HCID 178428661HCID 178428661, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3.5 g of ethyl 1-[N2 -(2-phenoxathiinylsulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylate in 15 ml of methanol and 10 ml of 2N-NaOH solution was warmed to 30° 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, H+ 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 ether to give 1.0 g of 1-[N2 -(2-phenoxathiinylsulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid as an amorphous solid. I.R. (KBr): 3400, 1625, 1460, 1165 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, H+ 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 ether

Sources & evidence

ORD record
ord-047aab704e73436a836d2191650e5c2e
Source dataset
uspto-grants-1978_12
Patent number
US04131673

Reaction notes

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