Acetic Acid → HCID 135438489, compound

HRID 227444Notes

Reaction equation

HRID 227444 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:41])[C:5]2[S:10][C:9](=[O:11])[N:8]([C@@H:12]3[O:29][C@H:28]([CH2:30][O:31]C(=O)C4C=CC=CC=4)[C@@:23]([CH3:40])([O:24]C(=O)C)[C@H:13]3[O:14]C(=O)C3C=CC=CC=3)[C:6]=2[N:7]=1.C([O-])([O-])=O.[K+].[K+].C(O)(=O)C>CO>[NH2:1][C:2]1[NH:3][C:4](=[O:41])[C:5]2[S:10][C:9](=[O:11])[N:8]([C@@H:12]3[O:29][C@H:28]([CH2:30][OH:31])[C@@:23]([CH3:40])([OH:24])[C@H:13]3[OH:14])[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 136131609HCID 136131609, compound

Product 1

HCID 135438489HCID 135438489, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Nucleoside triester 116 (100 mg, 0.172 mmol) was dissolved in methanol (5 mL) and K2CO3 (28.6 mg, 0.207 mmol) was added. The reaction progressed for 16 h. The reaction was neutralized with acetic acid (24.8 mg, 0.412 mmol). Then the solvent removed by rotary vacuum and the solid submitted to HPLC purification (MeCN—H2O) yielding 42 mg (74%) of white solid: 1H NMR (400 Mz, d6-DMSO) δ 11.20 (s, 1H), 6.89 (br s, 2H), 5.80 (d, J=8.0, 1H), 5.36 (d, J=6.0, 1H), 4.77 (t, J=8.0, 1H), 4.62 (s, 1H), 4.48 (m, 1H), 3.75 (m, 1H), 3.58-3.44 (m, 2H), 1.19 (s, 3H); Analysis calc'd for C14H14N4O6S.0.125H2O.0.125HCO2H: C, 39.33; H, 4.34; N, 16.43; S, 9.40. Found: C, 39.77; H, 4.81; N, 15.02; S, 9.69; [M+H]+ m/z 331.

Workup

  1. customThen the solvent removed by rotary vacuum
  2. customthe solid submitted to HPLC purification (MeCN—H2O)

Sources & evidence

ORD record
ord-07e2072b4028479a9a974659f0cd2a13
Source dataset
uspto-grants-2009_07
Patent number
US07560544B2

Reaction notes

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