Acetic Acid → HCID 178492899, compound

HRID 1390813Notes

Reaction equation

HRID 1390813 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:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)[CH:25]=1)(=[O:23])=[O:22])[CH2:12][CH:13]1[O:17][CH2:16][CH2:15][CH2:14]1)C1C=CC=CC=1.C(O)(=O)C.O.[H][H]>C(O)C.[Pd]>[N:20]#[N:38].[CH:32]1([C:26]2[CH:25]=[C:24]([S:21]([NH:20][C@H:19]([C:18]([N:11]([CH2:12][CH:13]3[O:17][CH2:16][CH2:15][CH2:14]3)[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:23])=[O:22])[CH:29]=[CH:28][C:27]=2[O:30][CH3:31])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 178418361HCID 178418361, compoundHCID 178492898HCID 178492898, compound

Product 1

HCID 178492899HCID 178492899, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2.4 g of NG -nitro-N2 -(3-cyclohexyl-4-methoxyphenylsulfonyl)-L-arginyl-N-tetrahydrofurfurylglycine 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 1.1 g (57%) of N2 -(3-cyclohexyl-4-methoxyphenylsulfonyl)-L-arginyl-N-tetrahydrofurfurylglycine 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 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-f360e8792e62454a8cbf1a8f61117cec
Source dataset
uspto-grants-1979_02
Patent number
US04140681

Reaction notes

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