Diazomethane → HCID 22880806, compound

HRID 965330Notes

Reaction equation

HRID 965330 reaction equation
[I:1][C:2]1[N:3]=[C:4]([NH2:20])[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11].O.O.[Sn](Cl)(Cl)(Cl)Cl.CO.[N+](=[CH2:32])=[N-]>COCCOC>[I:1][C:2]1[N:3]=[C:4]([NH2:20])[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[O:11][CH3:32].[I:1][C:2]1[N:3]=[C:4]([NH2:20])[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([O:13][CH3:32])[C@H:10]1[OH:11]

Participants

6

Reactant 3

HCID 9550DiazomethaneHCID 1696622-IodoadenosineHCID 86751834HCID 86751834, compound

Product 2

HCID 22880806HCID 22880806, compoundHCID 22880825HCID 22880825, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

1.2 g of 2-iodoadenosine was suspended in 150 ml of 1 mmol tin chloride dihydrate/methanol. 50 ml of 0.4-0.5M diazomethane in 1,2-dimethoxyethane was added with stirring. After stirring for one hour at room temperature, the reaction mixture was concentrated to dryness under reduced pressure. The resulting product was applied on ODS column and eluted with 40% (V/V) methanol in 0.1% (V/V) aqueous solution of TFA. First, 2-iodo-2'O-methyladenosine (Compound 47) was eluted, and then 2-iodo-3'-O-methyladenosine (Compound 48) was eluted. Both fractions were concentrated to dryness to give 135 mg of Compound 47 and 56 mg of Compound 48.

Workup

  1. stirringAfter stirring for one hour at room temperature
  2. concentrationthe reaction mixture was concentrated to dryness under reduced pressure
  3. washeluted with 40% (V/V) methanol in 0.1% (V/V) aqueous solution of TFA
  4. washFirst, 2-iodo-2'O-methyladenosine (Compound 47) was eluted
  5. wash2-iodo-3'-O-methyladenosine (Compound 48) was eluted
  6. concentrationBoth fractions were concentrated to dryness

Sources & evidence

ORD record
ord-571240fb1951495b9c6ea0a5642bcf68
Source dataset
uspto-grants-1998_06
Patent number
US05773603

Reaction notes

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