Acetic Acid → Phthalimidine

HRID 1862090Notes

Reaction equation

HRID 1862090 reaction equation
[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][NH:2]1.C1CCC(N=C=[N:19][CH:20]2CCCCC2)CC1.O[N:27]1[C:31](=O)[CH2:30][CH2:29][C:28]1=[O:33].[CH:34](N(C(C)C)CC)(C)C.[NH2:43][C:44]([NH2:46])=O.[C:47]([OH:50])(=[O:49])[CH3:48].CN([CH:54]=[O:55])C>>[CH3:48][C:47]1([CH3:34])[O:50][CH:30]2[CH:29]([CH:28]([CH2:54][OH:55])[O:33][CH:31]2[N:27]2[C:9]3[N:43]=[CH:44][N:46]=[C:3]([NH2:2])[C:4]=3[N:19]=[CH:20]2)[O:49]1.[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][NH:2]1

Participants

9

Reactant 7

HCID 176Acetic AcidHCID 1176UreaHCID 6228DimethylformamideHCID 10199PhthalimidineHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 81531Diisopropylethylamine2×

Product 2

HCID 10199PhthalimidineHCID 2321792',3'-O-Isopropylideneadenosine

Procedure

Compound 73 (32 gm, 0.1 mol) was added to a well stirred suspension of 2′,3′-isopropylidene adenosine-5′-carboxylic acid (36.5 gm, 0.11 mol), DCC (24.5 gm, 0.118 mol), N-hydroxy-succinimide (11.87 gm, 0.11 mol) in DMF (200 ml), and was followed by the addition of diisopropyl ethylamine (40 ml, 0.22 mol) at room temperature. The reaction mixture became clear after the addition of diisopropyl ethylamine, and urea started precipitating after some time. The reaction was left at room temperature for 3 days. The white precipitate of urea was filtered and washed thoroughly with DMF. The filtrate was concentrated under vacuum to remove diisopropyl ethylamine, and then treated with acetic acid (2 eq.) to break the DCC complex. Again, the solid was filtered and discarded. The filtrate was concentrated under high vacuum at 60° C., and the residue was purified on the silica gel column using 8% CH3OH—CH2Cl2 to give a of 2′,3′-isopropylidene adenosine protected derivative of compound 130.

Workup

  1. customstarted precipitating after some time
  2. filtrationThe white precipitate of urea was filtered
  3. washwashed thoroughly with DMF
  4. concentrationThe filtrate was concentrated under vacuum
  5. customto remove diisopropyl ethylamine
  6. filtrationAgain, the solid was filtered
  7. concentrationThe filtrate was concentrated under high vacuum at 60° C.
  8. customthe residue was purified on the silica gel column

Sources & evidence

ORD record
ord-a4e4fbe58e764d13ae11ce3164432523
Source dataset
uspto-grants-2003_03
Patent number
US06534651B2

Reaction notes

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