Acetic Acid → HCID 178472726, compound

HRID 973205Notes

Reaction equation

HRID 973205 reaction equation
[CH2:1]([O:3][C:4](=[O:42])[CH2:5][N:6]([C:11](=[O:41])[C@H:12]([CH2:34][CH2:35][CH2:36][NH:37][C:38](=[NH:40])[NH2:39])[N:13]([N+:31]([O-])=O)[S:14]([C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][C:21]([O:29][CH3:30])=[C:22]([O:27][CH3:28])[CH:23]=2)[CH:18]=1)(=[O:16])=[O:15])[CH2:7][CH2:8][O:9][CH3:10])[CH3:2].C(O)(=O)C.[H][H]>C(O)C.[Pd]>[N:13]#[N:31].[CH2:1]([O:3][C:4](=[O:42])[CH2:5][N:6]([C:11](=[O:41])[C@H:12]([CH2:34][CH2:35][CH2:36][NH:37][C:38](=[NH:39])[NH2:40])[NH:13][S:14]([C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][C:21]([O:29][CH3:30])=[C:22]([O:27][CH3:28])[CH:23]=2)[CH:18]=1)(=[O:16])=[O:15])[CH2:7][CH2:8][O:9][CH3:10])[CH3:2]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 178418361HCID 178418361, compoundHCID 178472725HCID 178472725, compound

Product 1

HCID 178472726HCID 178472726, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3.00 g of NG -nitro-N2 -(6,7-dimethoxy-2-naphthalenesulfonyl)-L-arginyl-N-(2-methoxyethyl)glycine ethyl 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 give an oily product. Reprecipitation with ethanoldiethyl ether gave 2.53 g (91%) of N2 -(6,7-dimethoxy-2-naphthalenesulfonyl)-L-arginyl-N-(2-methoxyethyl)glycine ethyl ester.

Workup

  1. filtrationAt the end of this period, the ethanol solution was filtered
  2. customto remove the catalyst
  3. customevaporated
  4. customto give an oily product
  5. customReprecipitation with ethanoldiethyl ether

Sources & evidence

ORD record
ord-d749115414194f668ba9146e5706180a
Source dataset
uspto-grants-1977_10
Patent number
US04055636

Reaction notes

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