HCID 178472718, compound → HCID 178486645, compound

HRID 616360Notes

Reaction equation

HRID 616360 reaction equation
[N:1]#[N:2].C([O:5][C:6](=[O:42])[CH2:7][N:8]([C:14](=[O:41])[C@H:15]([CH2:34][CH2:35][CH2:36][NH:37][C:38](=[NH:40])[NH2:39])[NH:16][S:17]([C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][C:24]([O:32][CH3:33])=[C:25]([O:30][CH3:31])[CH:26]=2)[CH:21]=1)(=[O:19])=[O:18])[CH2:9][CH:10]([O:12][CH3:13])[CH3:11])C>CO.[OH-].[Na+]>[N:1]#[N:2].[CH3:31][O:30][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][C:24]=1[O:32][CH3:33])[CH:21]=[C:20]([S:17]([NH:16][C@H:15]([C:14]([N:8]([CH2:9][CH:10]([O:12][CH3:13])[CH3:11])[CH2:7][C:6]([OH:42])=[O:5])=[O:41])[CH2:34][CH2:35][CH2:36][NH:37][C:38](=[NH:39])[NH2:40])(=[O:18])=[O:19])[CH:29]=[CH:28]2

Participants

4

Reactant 1

HCID 178472718HCID 178472718, compound

Product 1

HCID 178486645HCID 178486645, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 2.3 g of N2 -(6, 7-dimethoxy-2-naphthylsulfonyl)-L-arginyl-N-(2-methoxypropyl)glycine ethyl ester in 15 ml of methanol and 5 ml of 2N sodium hydroxide solution was warmed at 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 ether to give 1.8 g of N2 -(6, 7-dimethoxy-2-naphthylsulfonyl)L-arginyl-N-(2-methoxypropyl)glycine as an amorphous solid.

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-b688c807360e4698aa7071258269688f
Source dataset
uspto-grants-1978_02
Patent number
US04073892

Reaction notes

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