Sodium Hydroxide → HCID 178514626, compound

HRID 1390812Notes

Reaction equation

HRID 1390812 reaction equation
[N:1]#[N:2].C([O:5][C:6](=[O:43])[CH2:7][N:8]([C:15](=[O:42])[C@H:16]([CH2:35][CH2:36][CH2:37][NH:38][C:39](=[NH:41])[NH2:40])[NH:17][S:18]([C:21]1[CH:34]=[CH:33][C:32]2[O:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[S:24][C:23]=2[CH:22]=1)(=[O:20])=[O:19])[CH2:9][CH:10]1[O:14][CH2:13][CH2:12][CH2:11]1)C.[OH-].[Na+]>CO>[N:1]#[N:2].[CH:22]1[C:23]2[S:24][C:25]3[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:31][C:32]=2[CH:33]=[CH:34][C:21]=1[S:18]([NH:17][C@H:16]([C:15]([N:8]([CH2:9][CH:10]1[O:14][CH2:13][CH2:12][CH2:11]1)[CH2:7][C:6]([OH:43])=[O:5])=[O:42])[CH2:35][CH2:36][CH2:37][NH:38][C:39](=[NH:40])[NH2:41])(=[O:19])=[O:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178472694HCID 178472694, compound

Product 1

HCID 178514626HCID 178514626, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4.8 g of N2 -(2-phenoxathiinylsulfonyl)-L-arginyl-N-tetrahydrofurfurylglycine 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, 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 ethyl ether to give 3.2 g (80 percent) of N2 -(2-phenoxathiinylsulfonyl)-L-arginyl-N-tetrahydrofurfurylglycine as an amorphous solid. I.R. (KBr): 3350, 1640, 1250 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 ethyl ether

Sources & evidence

ORD record
ord-8883017d45624f4aa93ddfb6f7388ac1
Source dataset
uspto-grants-1979_02
Patent number
US04140681

Reaction notes

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