[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-(4-Nitro-2-sulfobenzamido)-2-sulfobenzamido]-1,3,6-naphthalenetrisulfonic acid

HRID 2166508Notes

Reaction equation

HRID 2166508 reaction equation
[NH2:1][C:2]1[CH:32]=[CH:31][C:5]([C:6]([NH:8][C:9]2[CH:10]=[C:11]([S:27]([OH:30])(=[O:29])=[O:28])[CH:12]=[C:13]3[C:18]=2[C:17]([S:19]([OH:22])(=[O:21])=[O:20])=[CH:16][C:15]([S:23]([OH:26])(=[O:25])=[O:24])=[CH:14]3)=[O:7])=[C:4]([S:33]([OH:36])(=[O:35])=[O:34])[CH:3]=1.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.O.O.C([O-])(=O)C.[Na+].[N+](C1C=CC(C([O:106][C:107](=O)[C:108]2[CH:113]=[CH:112][C:111]([N+:114]([O-:116])=[O:115])=[CH:110][C:109]=2[S:117]([OH:120])(=[O:119])=[O:118])=O)=C(S(O)(=O)=O)C=1)([O-])=O>O>[N+:114]([C:111]1[CH:112]=[CH:113][C:108]([C:107]([NH:1][C:2]2[CH:32]=[CH:31][C:5]([C:6]([NH:8][C:9]3[CH:10]=[C:11]([S:27]([OH:30])(=[O:28])=[O:29])[CH:12]=[C:13]4[C:18]=3[C:17]([S:19]([OH:22])(=[O:21])=[O:20])=[CH:16][C:15]([S:23]([OH:26])(=[O:24])=[O:25])=[CH:14]4)=[O:7])=[C:4]([S:33]([OH:36])(=[O:35])=[O:34])[CH:3]=2)=[O:106])=[C:109]([S:117]([OH:120])(=[O:118])=[O:119])[CH:110]=1)([O-:116])=[O:115]

Participants

6

Reactant 4

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 131521228-(4-Amino-2-sulfobenzamido)-1,3,6-naphthalenetrisulfonic acidHCID 23665404Sodium Acetate TrihydrateHCID 570029234-Nitro-2-sulfobenzoic anhydride

Product 1

HCID 131521248-[4-(4-Nitro-2-sulfobenzamido)-2-sulfobenzamido]-1,3,6-naphthalenetrisulfonic acidYield 165.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an ice-cold solution of 17.2 g of 8-(4-amino-2-sulfobenzamido)-1,3,6-naphthalenetrisulfonic acid, tetrasodium salt, and 5.24 g of sodium acetate trihydrate in 100 ml of water was added 6.87 g of 4-nitro-2-sulfobenzoic anhydride. The mixture was stirred for 10 minutes, and filtered through diatomaceous earth. The filtrate was poured into 750 ml of absolute ethanol with vigorous stirring and cooled in an ice bath. The solid was recovered by filtration, washed with ethanol and ether and evaporated in vacuo overnight. This solid was dissolved in 100 ml of water, acidified with 3 ml of concentrated hydrochloric acid, and then poured with vigorous stirring into 500 ml of cold absolute ethanol. The solid was collected by filtration, washed with ethanol, then ether, and dried overnight at 110° C., giving 19.35 g of 8-[4-(4-nitro-2-sulfobenzamido)-2-sulfobenzamido]-1,3,6-naphthalenetrisulfonic acid, pentasodium salt as a powder.

Workup

  1. filtrationfiltered through diatomaceous earth
  2. additionThe filtrate was poured into 750 ml of absolute ethanol
  3. stirringwith vigorous stirring
  4. temperaturecooled in an ice bath
  5. filtrationThe solid was recovered by filtration
  6. washwashed with ethanol and ether
  7. customevaporated in vacuo overnight
  8. dissolutionThis solid was dissolved in 100 ml of water
  9. additionpoured
  10. stirringwith vigorous stirring into 500 ml of cold absolute ethanol
  11. filtrationThe solid was collected by filtration
  12. washwashed with ethanol
  13. dry with materialether, and dried overnight at 110° C.

Sources & evidence

ORD record
ord-b096264a9dc14e81ac8e3164a3444339
Source dataset
uspto-grants-1983_06
Patent number
US04387059

Reaction notes

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