HCID 178470102, compound → HCID 178487528, compound

HRID 839582Notes

Reaction equation

HRID 839582 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([S:13]([NH:16][C@H:17]([C:25]([N:27]3[CH2:32][CH2:31][S:30][CH2:29][CH:28]3[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:10]2)=[CH:5][CH:4]=1>CO.[OH-].[Na+]>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([S:13]([NH:16][C@H:17]([C:25]([N:27]3[CH2:32][CH2:31][S:30][CH2:29][CH:28]3[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:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 178470102HCID 178470102, compound

Product 1

HCID 178487528HCID 178487528, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 2 g of ethyl 4-[N2 -(7-methoxy-2-naphthalenesulfonyl)-L-arginyl]thiomorpholine-3-carboxylate in 15 ml of methanol and 4 ml of 2N sodium hydroxide solution was warmed to 50° C and held at that temperature for 24 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 1.3 g of 4-[N2 -(7-methoxy-2-naphthalenesulfonyl)-L-arginyl]thiomorpholine-3-carboxylic acid.

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-ff1743e018714e558f99c2ca4779849f
Source dataset
uspto-grants-1978_06
Patent number
US04096255

Reaction notes

Loading…