Acetic Acid → HCID 178486641, compound

HRID 441594Notes

Reaction equation

HRID 441594 reaction equation
C([O:8][C:9](=[O:49])[CH2:10][N:11]([C:18](=[O:48])[C@H:19]([CH2:41][CH2:42][CH2:43][NH:44][C:45](=[NH:47])[NH2:46])[N:20]([N+:38]([O-])=O)[S:21]([C:24]1[CH:33]=[CH:32][C:31]2[C:26](=[CH:27][C:28]([O:36][CH3:37])=[C:29]([O:34][CH3:35])[CH:30]=2)[CH:25]=1)(=[O:23])=[O:22])[CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)C1C=CC=CC=1.C(O)(=O)C.[H][H]>C(O)C.[Pd]>[N:20]#[N:38].[CH3:35][O:34][C:29]1[CH:30]=[C:31]2[C:26](=[CH:27][C:28]=1[O:36][CH3:37])[CH:25]=[C:24]([S:21]([NH:20][C@H:19]([C:18]([N:11]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[CH2:10][C:9]([OH:49])=[O:8])=[O:48])[CH2:41][CH2:42][CH2:43][NH:44][C:45](=[NH:46])[NH2:47])(=[O:22])=[O:23])[CH:33]=[CH:32]2

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 178418361HCID 178418361, compoundHCID 178486642HCID 178486642, compound

Product 1

HCID 178486641HCID 178486641, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To a solution of 3.00 of NG -nitro-N2 -(6,7-dimethoxy-2-naphthalenesulfonyl)-L-arginyl-N-cyclohexylglycine 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 filtred 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 1.65 g (68%) of N2 -(6,7-dimethoxy-2-naphthalenesulfonyl)-L-arginyl-N-cyclohexylglycine as an amorphous solid.

Workup

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

Sources & evidence

ORD record
ord-c49bac61f651491e9422753ba92c7654
Source dataset
uspto-grants-1977_08
Patent number
US04041156

Reaction notes

Loading…