Acetic Acid → HCID 178514624, compound

HRID 1834502Notes

Reaction equation

HRID 1834502 reaction equation
C([O:8][C:9](=[O:46])[CH2:10][N:11]([C:19](=[O:45])[C@H:20]([CH2:38][CH2:39][CH2:40][NH:41][C:42](=[NH:44])[NH2:43])[N:21]([N+:35]([O-])=O)[S:22]([C:25]1[CH:34]=[CH:33][C:32]2[CH2:31][CH2:30][CH2:29][CH2:28][C:27]=2[CH:26]=1)(=[O:24])=[O:23])[CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)C1C=CC=CC=1.C(O)(=O)C.[H][H]>C(O)C.[Pd]>[N:21]#[N:35].[CH:26]1[C:27]2[CH2:28][CH2:29][CH2:30][CH2:31][C:32]=2[CH:33]=[CH:34][C:25]=1[S:22]([NH:21][C@H:20]([C:19]([N:11]([CH2:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1)[CH2:10][C:9]([OH:46])=[O:8])=[O:45])[CH2:38][CH2:39][CH2:40][NH:41][C:42](=[NH:43])[NH2:44])(=[O:23])=[O:24]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 178418361HCID 178418361, compoundHCID 178512836HCID 178512836, compound

Product 1

HCID 178514624HCID 178514624, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3.00 g of NG -nitro-N2 -(5,6,7,8-tetrahydro-2-naphthalenesulfonyl)-L-arginyl-N-cyclohexylmethylglycine 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 solution was evaporated to dryness to give 2.07 g (87%) of N2 -(5,6,7,8-tetrahydro-2-naphthalenesulfonyl)-L-arginyl-N-cyclohexylmethylglycine as a powder.

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 solution
  9. customwas evaporated to dryness

Sources & evidence

ORD record
ord-9210c292ee184b4387cd7334ef8ec68a
Source dataset
uspto-grants-1978_01
Patent number
US04070457

Reaction notes

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