Ethanol → HCID 178460214, compound

HRID 1032038Notes

Reaction equation

HRID 1032038 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:27]/[O:28][C:29]([C:32]([O:34]CC2C=CC([N+]([O-])=O)=CC=2)=[O:33])([CH3:31])[CH3:30])/[C:8]([NH:10][C@@H:11]2[C:21](=[O:22])[N:20]3[C@@H:12]2[CH2:13][S:14][C@H:15]2[C@@:19]3([C:23]([O-:25])=[O:24])[O:18][C:17](=[O:26])[CH2:16]2)=[O:9])[N:6]=1.[Na+:45].P([O-])([O-])([O-])=O.C(O)C.[H][H]>O.[C].[Pd]>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:27]/[O:28][C:29]([C:32]([OH:34])=[O:33])([CH3:31])[CH3:30])/[C:8]([NH:10][C@@H:11]2[C:21](=[O:22])[N:20]3[C@@H:12]2[CH2:13][S:14][C@H:15]2[C@@:19]3([C:23]([O-:25])=[O:24])[O:18][C:17](=[O:26])[CH2:16]2)=[O:9])[N:6]=1.[Na+:45]

Participants

7

Reactant 4

HCID 702EthanolHCID 1061PhosphateHCID 15117570HCID 15117570, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 178460214HCID 178460214, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 962WaterSolvent

Procedure

In 5 ml of water was dissolved 0.148 g of the compound obtained in Example 7. To this solution were added 5 ml of a 0.1 M phosphate buffer solution, 5 ml of ethanol and 0.075 g of 10% palladium-carbon. Into the mixture was introduced hydrogen gas while stirring under ice-cooling. In 1.5 hour after starting of the reaction, 0.04 g of 10% palladium-carbon was added to the reaction system, followed by stirring for further one hour. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure to a volume of about 5 ml. The residue was subjected to a Amberlite XAD-2 column chromatography. Fractions eluted with water were combined and freeze-dried to give 0.091 g of the subject compound as powders.

Workup

  1. temperaturecooling
  2. additionwas added to the reaction system
  3. stirringby stirring for further one hour
  4. filtrationThe catalyst was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure to a volume of about 5 ml
  6. washFractions eluted with water
  7. customfreeze-dried

Sources & evidence

ORD record
ord-209d29ada4294a03a9ca20c9ed7c82e6
Source dataset
uspto-grants-1990_09
Patent number
US04956358

Reaction notes

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