Acetic Acid → HCID 178486636, compound

HRID 1834194Notes

Reaction equation

HRID 1834194 reaction equation
C([O:8][C:9](=[O:51])[CH2:10][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.C(O)(=O)C.[H][H]>C(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)[CH2:10][C:9]([OH:51])=[O:8])=[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

6

Reactant 3

HCID 176Acetic AcidHCID 178418361HCID 178418361, compoundHCID 178486637HCID 178486637, compound

Product 1

HCID 178486636HCID 178486636, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3.00 g of NG -nitro-N2 -(6,7-dimethoxy-2-naphthalenesulfonyl)-L-arginyl-N-phenethylglycine benzyl ester in 50 ml of ethanol and 0.5 ml of acetic acid was added 0.5 g 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 1.71 g (70%) of N2 -(6,7-dimethoxy-2-naphthalenesulfonyl)-L-arginyl-N-phenethylglycine 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-d35bbcb99b37449296e435b16dd4f134
Source dataset
uspto-grants-1978_01
Patent number
US04069318

Reaction notes

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