[2-adenin-9-yl-5-[[[[5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-oxido-phosphoryl]oxy-oxido-phosphoryl]oxymethyl]-4-hydroxy-tetrahydrofuran-3-yl] phosphate → 8-(4-Amino-2-sulfobenzamido)-1,3,6-naphthalenetrisulfonic acid

HRID 2166507Notes

Reaction equation

HRID 2166507 reaction equation
[N+:1]([C:4]1[CH:34]=[CH:33][C:7]([C:8]([NH:10][C:11]2[CH:12]=[C:13]([S:29]([OH:32])(=[O:31])=[O:30])[CH:14]=[C:15]3[C:20]=2[C:19]([S:21]([OH:24])(=[O:23])=[O:22])=[CH:18][C:17]([S:25]([OH:28])(=[O:27])=[O:26])=[CH:16]3)=[O:9])=[C:6]([S:35]([OH:38])(=[O:37])=[O:36])[CH:5]=1)([O-])=O.C1C(C(N)=O)=CN(C2OC(COP(OP(OCC3OC(N4C5N=CN=C(N)C=5N=C4)C(OP([O-])([O-])=O)C3O)([O-])=O)([O-])=O)C(O)C2O)C=C1.[Na+].[Na+].[Na+].[Na+]>O.[Pd]>[NH2:1][C:4]1[CH:34]=[CH:33][C:7]([C:8]([NH:10][C:11]2[CH:12]=[C:13]([S:29]([OH:32])(=[O:30])=[O:31])[CH:14]=[C:15]3[C:20]=2[C:19]([S:21]([OH:24])(=[O:23])=[O:22])=[CH:18][C:17]([S:25]([OH:28])(=[O:26])=[O:27])=[CH:16]3)=[O:9])=[C:6]([S:35]([OH:38])(=[O:37])=[O:36])[CH:5]=1

Participants

5

Reactant 2

HCID 12598259[2-adenin-9-yl-5-[[[[5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-oxido-phosphoryl]oxy-oxido-phosphoryl]oxymethyl]-4-hydroxy-tetrahydrofuran-3-yl] phosphateHCID 131521208-(4-Nitro-2-sulfobenzamido)-1,3,6-naphthalenetrisulfonic acid

Product 1

HCID 131521228-(4-Amino-2-sulfobenzamido)-1,3,6-naphthalenetrisulfonic acidYield 89.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of 42.4 g of 8-(4-nitro-2-sulfobenzamido)-1,3,6-naphthalenetrisulfonic acid, tetrasodium salt, and 1.5 g of 10% palladium-on-carbon in 150 ml of water was hydrogenated in a Parr shaker for one hour. The mixture was filtered through diatomaceous earth. The filtrate was concentrated to about 130 ml and poured with vigorous stirring into 500 ml of absolute ethanol. The resulting gum was collected by filtration through diatomaceous earth and then dissolved from the diatomaceous earth with water. The aqueous solution was concentrated to 15 ml and then diluted with 85 ml of ethanol giving a gum which was stirred with absolute ethanol giving a solid which was dried overnight in a pistol at 110° C. giving 36.15 g of 8-(4-amino-2-sulfobenzamido)-1,3,6-naphthalenetrisulfonic acid, tetrasodium salt.

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth
  2. concentrationThe filtrate was concentrated to about 130 ml
  3. additionpoured
  4. filtrationThe resulting gum was collected by filtration through diatomaceous earth
  5. dissolutiondissolved from the diatomaceous earth with water
  6. concentrationThe aqueous solution was concentrated to 15 ml
  7. additiondiluted with 85 ml of ethanol giving a gum which
  8. stirringwas stirred with absolute ethanol giving a solid which
  9. customwas dried overnight in a pistol at 110° C.

Sources & evidence

ORD record
ord-213c25c3a3dc4aa5ad34bfac8ec41d8b
Source dataset
uspto-grants-1983_06
Patent number
US04387059

Reaction notes

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