Acetic Acid → HCID 136008333, compound

HRID 1534952Notes

Reaction equation

HRID 1534952 reaction equation
N[CH:2]1[NH:10][CH:9]=[N:8][C:7]2[N:6]([CH2:11][CH:12]([CH2:17][C:18]([O:20]C)=[O:19])[C:13]([O:15]C)=[O:14])[CH:5]=[N:4][C:3]1=2.C(O)(=[O:24])C.N([O-])=O.[Na+].C(OCC)C>O>[O:24]=[C:2]1[NH:10][CH:9]=[N:8][C:7]2[N:6]([CH2:11][CH:12]([C:13]([OH:15])=[O:14])[CH2:17][C:18]([OH:20])=[O:19])[CH:5]=[N:4][C:3]1=2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 23668193Sodium Nitrite2×HCID 178500491HCID 178500491, compound

Product 1

HCID 136008333HCID 136008333, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

2.00 g (6.82 mmol) of 2-[(1,6-dihydro-6-amino-9H-purin-9-yl)methyl]butanedioic acid, dimethyl ester (AIT-0073) was placed into a 50 ml round bottom flask equipped with a magnetic stirring bar. Then 10 ml glacial acetic acid was added and the solution was stirred until homogeneous. 2.35 g (34.10 mmol) of NaNO2 in 4 ml of H2O was added to the stirring solution dropwise. The stoppered solution was stirred for 24 hours at room temperature. An additional 0.775 g (11.23 mmol) of NaNO2 in 1 ml H2O was added and the solution was stirred for another 24 hours. The acetic acid was removed under reduced pressure on the rotary evaporator. Water was added and was removed in the same manner. This was repeated again until little or no more acetic acid was left. 10 ml of H2O was added to the semi-solid residue to completely dissolve the mixture. This solution was extracted with 30 ml-40 ml of acetonitrile and the aqueous layer was discarded. The organic layer was washed twice with 30 ml of saturated brine. Upon evaporation of the solvent, a light orange oil was obtained. This was treated with 35 ml of ethyl ether and triturated with methanol to yield 615 mg of 3-[(1,6-dihydro-6-oxo-9H-purin-9-yl)methyl]butanedioicacid, methyl diester (AIT-0075) as an off-white solid. Yield: 31% m.p. 130°-135° C.

Workup

  1. customequipped with a magnetic stirring bar
  2. stirringThe stoppered solution was stirred for 24 hours at room temperature
  3. stirringthe solution was stirred for another 24 hours
  4. customThe acetic acid was removed under reduced pressure on the rotary evaporator
  5. additionWater was added
  6. customwas removed in the same manner
  7. waitwas left
  8. addition10 ml of H2O was added to the semi-solid residue
  9. dissolutionto completely dissolve the mixture
  10. extractionThis solution was extracted with 30 ml-40 ml of acetonitrile
  11. washThe organic layer was washed twice with 30 ml of saturated brine
  12. customUpon evaporation of the solvent
  13. customa light orange oil was obtained
  14. customtriturated with methanol

Sources & evidence

ORD record
ord-dfc2a8c8a7924af5a4d34dc623ec66f7
Source dataset
uspto-grants-1992_02
Patent number
US05091432

Reaction notes

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