HCID 178472541, compound → HCID 178486640, compound

HRID 2420120Notes

Reaction equation

HRID 2420120 reaction equation
[N:1]#[N:2].C([O:5][C:6](=[O:45])[C@H:7]([CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[N:8]([C:10](=[O:37])[C@H:11]([CH2:30][CH2:31][CH2:32][NH:33][C:34](=[NH:36])[NH2:35])[NH:12][S:13]([C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][C:20]([O:28][CH3:29])=[C:21]([O:26][CH3:27])[CH:22]=2)[CH:17]=1)(=[O:15])=[O:14])[CH3:9])C>C(O)C.[OH-].[Na+]>[N:1]#[N:2].[CH3:27][O:26][C:21]1[CH:22]=[C:23]2[C:18](=[CH:19][C:20]=1[O:28][CH3:29])[CH:17]=[C:16]([S:13]([NH:12][C@H:11]([C:10]([N:8]([CH3:9])[C@H:7]([C:6]([OH:45])=[O:5])[CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)=[O:37])[CH2:30][CH2:31][CH2:32][NH:33][C:34](=[NH:35])[NH2:36])(=[O:14])=[O:15])[CH:25]=[CH:24]2

Participants

4

Reactant 1

HCID 178472541HCID 178472541, compound

Product 1

HCID 178486640HCID 178486640, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 2.5 g of N2 -(6,7-dimethoxy-2-naphthylsulfonyl)-L-arginyl-N-methylphenylalanine 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 1.86 g (78 percent) of N2 -(6,7-dimethoxy-2-naphthyl-sulfonyl)-L-arginyl-N-methylphenylalanine as an amorphous solid, I.R. (KBr): 3,300 (broad), 1,600 cm-1

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-2a0f52bc95494a90a1c603e47b4c99dd
Source dataset
uspto-grants-1978_08
Patent number
US04108986

Reaction notes

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