HCID 178472728, compound → HCID 178495949, compound

HRID 616356Notes

Reaction equation

HRID 616356 reaction equation
[N:1]#[N:2].C([O:5][C:6](=[O:41])[CH2:7][N:8]([C:13](=[O:40])[C@H:14]([CH2:33][CH2:34][CH2:35][NH:36][C:37](=[NH:39])[NH2:38])[NH:15][S:16]([C:19]1[CH:28]=[C:27]([O:29][CH3:30])[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([O:31][CH3:32])[CH:25]=2)[CH:20]=1)(=[O:18])=[O:17])[CH2:9][CH2:10][O:11][CH3:12])C>C(O)C.[OH-].[Na+]>[N:1]#[N:2].[CH3:30][O:29][C:27]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([O:31][CH3:32])[CH:25]=2)[CH:20]=[C:19]([S:16]([NH:15][C@H:14]([C:13]([N:8]([CH2:9][CH2:10][O:11][CH3:12])[CH2:7][C:6]([OH:41])=[O:5])=[O:40])[CH2:33][CH2:34][CH2:35][NH:36][C:37](=[NH:38])[NH2:39])(=[O:18])=[O:17])[CH:28]=1

Participants

4

Reactant 1

HCID 178472728HCID 178472728, compound

Product 1

HCID 178495949HCID 178495949, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 2.5 g of N2 -(4, 6-dimethoxy-2-naphthylsulfonyl)-L-arginyl-N-(2-methoxyethyl)glycine ethyl ester in 5 ml of ethanol and 7 ml of 1N NaOH solution was stirred for 30 hours at room temperature. At the end of this period, the solution was concentrated to 5 ml, chromatographed on 80 ml of Daiaion® SK 102 ion exchange resin (200-300 mesh, H+ form, manufactured by Mitsubishi Chemical Industries Limited) packed in water, washed with water, and eluted with 3% ammonium hydroxide solution. The fraction eluted from 3% ammonium hydroxide solution was evaporated to dryness, and the residue was purified by reprecipitation with ethanol-diethyl ether to give 1.32 g (72 percent) of N2 -(4, 6-dimethoxy-2-naphthylsulfonyl)-L-arginyl-N-(2-methoxyethyl)glycine as an amorphous solid, I.R. (KBr): 3,360, 3,180, 1,610 cm-1. Analysis Calcd. for C23H33N5O8S (percent): C, 51.20; H, 6.17; N, 12.98 Found (percent): C, 51.31; H, 6.01; N, 12.67.

Workup

  1. concentrationAt the end of this period, the solution was concentrated to 5 ml
  2. customchromatographed on 80 ml of Daiaion® SK 102 ion exchange resin (200-300 mesh, H+ form, manufactured by Mitsubishi Chemical Industries Limited)
  3. washwashed with water
  4. washeluted with 3% ammonium hydroxide solution
  5. washThe fraction eluted from 3% ammonium hydroxide solution
  6. customwas evaporated to dryness
  7. customthe residue was purified by reprecipitation with ethanol-diethyl ether

Sources & evidence

ORD record
ord-d40d7be15d3340958730ad9a88e5ce46
Source dataset
uspto-grants-1978_02
Patent number
US04073892

Reaction notes

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