Acetic Acid → HCID 178472726, compound

HRID 616399Notes

Reaction equation

HRID 616399 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-naphthylsulfonyl)-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 ethanol-ethyl ether gave 2.53 g (91%) of N2 -(6,7-dimethoxy-2-naphthylsulfonyl)-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 ethanol-ethyl ether

Sources & evidence

ORD record
ord-9eeba2df890041378e70bfb3e74debf4
Source dataset
uspto-grants-1978_02
Patent number
US04073913

Reaction notes

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