Acetic Acid → HCID 178449160, compound

HRID 839913Notes

Reaction equation

HRID 839913 reaction equation
C([O:8][C:9](=[O:47])[CH2:10][N:11]([C:16](=[O:46])[C@H:17]([CH2:39][CH2:40][CH2:41][NH:42][C:43](=[NH:45])[NH2:44])[N:18]([N+:36]([O-])=O)[S:19]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[CH:23]=1)(=[O:21])=[O:20])[CH2:12][CH2:13][CH2:14][CH3:15])C1C=CC=CC=1.C(O)(=O)C.O.[H][H]>C(O)C.[Pd]>[N:18]#[N:36].[CH:30]1([C:24]2[CH:23]=[C:22]([S:19]([NH:18][C@H:17]([C:16]([N:11]([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:10][C:9]([OH:47])=[O:8])=[O:46])[CH2:39][CH2:40][CH2:41][NH:42][C:43](=[NH:44])[NH2:45])(=[O:21])=[O:20])[CH:27]=[CH:26][C:25]=2[O:28][CH3:29])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 178418361HCID 178418361, compoundHCID 178449144HCID 178449144, compound

Product 1

HCID 178449160HCID 178449160, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3.00 g of NG -nitro-N2 -(3-cyclohexyl-4-methoxyphenylsulfonyl)-L-arginyl-N-butylglycine benzyl ester in 50 ml of ethanol, 10 ml of acetic acid and 10 ml of water was added 0.5 g of palladium-black and then the mixture was shaken in a hydrogen atmosphere for 50 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, 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 1.5 g (72%) of N2 -(3-cyclohexyl-4-methoxyphenylsulfonyl)-L-arginyl-N-butylglycine as an amorphous solid. I.R. (KBr): 3,350, 2,920, 1,630, 1,250 cm-1

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 ethyl 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-589ef33a37e84d9c9afb9b0c7bd850bf
Source dataset
uspto-grants-1978_06
Patent number
US04097591

Reaction notes

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