Acetic Acid → HCID 136051363, compound

HRID 227439Notes

Reaction equation

HRID 227439 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:30])[C:5]2[S:10][C:9](=[S:11])[N:8]([C@@H:12]3[O:24][C@H:23]([CH2:25][O:26]C(=O)C)[C@@H:18]([O:19]C(=O)C)[C@H:13]3[O:14]C(=O)C)[C:6]=2[N:7]=1.C([O-])([O-])=O.[K+].[K+].CC(O)=O>CO>[NH2:1][C:2]1[NH:3][C:4](=[O:30])[C:5]2[S:10][C:9](=[S:11])[N:8]([C@@H:12]3[O:24][C@H:23]([CH2:25][OH:26])[C@@H:18]([OH:19])[C@H:13]3[OH:14])[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 135466563HCID 135466563, compound

Product 1

HCID 136051363HCID 136051363, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Nucleoside triester 32 (100 mg, 0.21 mmol) and K2CO3 (42.7 mg, 0.31 mmol) were dissolved in MeOH (5 mL) and stirred for 16 h at ambient temperature. To this mixture was added HOAc (37 mg, 0.62 mmol) and the solvent was removed via rotary evaporation. The residue were then submitted to HPLC purification (MeCN—H2O) yielding 47 mg (66%) of a solid: 1H NMR (400 MHz, d6-DMSO) δ 11.66 (s, 1H), 6.91 (br s, 2H), 6.47 (s, 1H), 5.31 (d, J=5.2, 1H), 4.94 (s, 1H), 4.78 (s, 2H), 4.27 (d, J=8.0, 1H), 3.78 (m, 1H), 3.69 (m, 1H), 3.52 (m, 1H); [M+H]+ m/z 333. Analysis calc'd for C10H12N4O5S2.0.5TFA•0.75H2O.0.25MeCN: C, 33.43; H, 3.60; N, 14.41. Found: C, 33.11; H, 3.73; N, 14.80.

Workup

  1. customthe solvent was removed via rotary evaporation
  2. customThe residue were then submitted to HPLC purification (MeCN—H2O)

Sources & evidence

ORD record
ord-3bb70510a0784d12bbd617921b319973
Source dataset
uspto-grants-2009_07
Patent number
US07560544B2

Reaction notes

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