Sodium Hydroxide → HCID 178495948, compound

HRID 839911Notes

Reaction equation

HRID 839911 reaction equation
[N:1]#[N:2].C([O:5][C:6](=[O:40])[CH2:7][N:8]([C:13](=[O:39])[C@H:14]([CH2:32][CH2:33][CH2:34][NH:35][C:36](=[NH:38])[NH2:37])[NH:15][S:16]([C:19]1[CH:31]=[CH:30][C:22]2[S:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:21]=2[CH:20]=1)(=[O:18])=[O:17])[CH2:9][CH2:10][O:11][CH3:12])C.[OH-].[Na+]>CO>[N:1]#[N:2].[CH:20]1[C:21]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[S:23][C:22]=2[CH:30]=[CH:31][C:19]=1[S:16]([NH:15][C@H:14]([C:13]([N:8]([CH2:9][CH2:10][O:11][CH3:12])[CH2:7][C:6]([OH:40])=[O:5])=[O:39])[CH2:32][CH2:33][CH2:34][NH:35][C:36](=[NH:37])[NH2:38])(=[O:17])=[O:18]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178472727HCID 178472727, compound

Product 1

HCID 178495948HCID 178495948, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5.5 g of N2 -(2-dibenzothienylsulfonyl)-L-arginyl-N-(2-methoxyethyl)glycine ethyl ester in 15 ml of methanol and 15 ml of 2N-NaOH solution was warmed to 40° 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 3.05 g (62 percent) of N2 -(2-dibenzothienylsulfonyl)-L-arginyl-N-(2-methoxyethyl)glycine as an amorphous solid. I.R. (KBr): 3,400, 1,630, 1,280 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-cc338200e58a4f46848211484fca623c
Source dataset
uspto-grants-1978_06
Patent number
US04097591

Reaction notes

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