HCID 178418361, compound → HCID 178486638, compound

HRID 2420117Notes

Reaction equation

HRID 2420117 reaction equation
C([O:8][C:9](=[O:52])[C@H:10]([CH3:51])[N:11]([C:20](=[O:50])[C@H:21]([CH2:43][CH2:44][CH2:45][NH:46][C:47](=[NH:49])[NH2:48])[N:22]([N+:40]([O-])=O)[S:23]([C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[CH:29][C:30]([O:38][CH3:39])=[C:31]([O:36][CH3:37])[CH:32]=2)[CH:27]=1)(=[O:25])=[O:24])[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)C1C=CC=CC=1.[H][H]>C(O)(=O)C.[Pd]>[N:22]#[N:40].[CH3:37][O:36][C:31]1[CH:32]=[C:33]2[C:28](=[CH:29][C:30]=1[O:38][CH3:39])[CH:27]=[C:26]([S:23]([NH:22][C@H:21]([C:20]([N:11]([CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C@H:10]([C:9]([OH:52])=[O:8])[CH3:51])=[O:50])[CH2:43][CH2:44][CH2:45][NH:46][C:47](=[NH:48])[NH2:49])(=[O:25])=[O:24])[CH:35]=[CH:34]2

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178486639HCID 178486639, compound

Product 1

HCID 178486638HCID 178486638, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 3.00 g of NG -nitro-N2 -(6,7-dimethoxy-2-naphthylsulfonyl)-L-arginyl-N-phenethylalanine benzyl ester in 50 ml of acetic acid was added 0.5 of palladium-black and then the mixture was shaken in a hydrogen atmosphere for 100 hours at room temperature. At the end of this period, the ethanol solution was filtered to remove the catalyst and evaporated to dryness. The residue was washed several times with dry diethyl ether and 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 was evaporated to dryness to give 1.64 g (67%) of N2 -(6,7-dimethoxy-2-naphthylsulfonyl)-L-arginyl-N-phenethylalanine as an amorphous solid.

Workup

  1. filtrationAt the end of this period, the ethanol solution was filtered
  2. customto remove the catalyst
  3. customevaporated to dryness
  4. washThe residue was washed several times with dry diethyl ether
  5. customchromatographed on 80 ml of Daiaion ®SK 102 ion exchange resin (200-300 mesh, H+ form, manufactured by Mitsubishi Chemical Industries Limited)
  6. washwashed with water
  7. washeluted with 3% ammonium hydroxide solution
  8. washThe fraction eluted from 3% ammonium hydroxide
  9. customwas evaporated to dryness

Sources & evidence

ORD record
ord-cd9c2a939f024e64be9033946ac30ee5
Source dataset
uspto-grants-1978_08
Patent number
US04108986

Reaction notes

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