Acetic Acid → HCID 178486636, compound

HRID 1764707Notes

Reaction equation

HRID 1764707 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, compound2×

Product 1

HCID 178486636HCID 178486636, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

NG -nitro-N2 -(6,7-dimethoxy-2-naphthylsulfonyl)-L-arginyl-N-phenethylglycine benzyl ester was prepared by the procedure described in Example 3, and has a melting point of 133°-5° C. To a solution of 3.00 g of NG -nitro-N2 -(6,7-dimethoxy-2-naphthylsulfonyl)-L-arginyl-N-phenethylglycine benzyl ester in 50 ml of ethanol and 0.5 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 ethyl ether and chromatographed on 80 ml of Daiaion ® SK 102 ion exchange resin (200 - 300 mesh, II+ 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 to give 1.71 g (70%) of N2 -(6,7-dimethoxy-2-naphthylsulfonyl)-L-arginyl-N-phenethylglycine as an amorphous solid.

Workup

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

Sources & evidence

ORD record
ord-b9023efeaebc43e485e0353d6720bfdf
Source dataset
uspto-grants-1978_09
Patent number
US04117127

Reaction notes

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