Acetic Acid → HCID 11709425, compound

HRID 420875Notes

Reaction equation

HRID 420875 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][C:9](=[O:11])[N:8]([C@@H:12]3[O:35][C@H:34]([CH2:36][O:37]C(=O)C4C=CC=CC=4)[C@@H:23]([O:24]C(=O)C4C=CC=CC=4C)[C@H:13]3[O:14]C(=O)C3C=CC=CC=3)[C:6]=2[N:7]=1.[C:46]([O-])([O-])=O.[K+].[K+].CC(O)=O>CO>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][C:9](=[O:11])[N:8]([C@@H:12]3[O:35][C@H:34]([CH2:36][OH:37])[C@@H:23]([OH:24])[C@@:13]3([CH3:46])[OH:14])[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 86606511HCID 86606511, compound

Product 1

HCID 11709425HCID 11709425, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of nucleoside 3 (380 mg, 0.606 mmol) in MeOH (20 mL) was added K2CO3 (17 mg, 0.12 mmol) at rt. The resulting mixture was stirred 18 h at rt whereupon it was treated with HOAc (15 μL, 0.25 mmol), concentrated and submitted to HPLC purification (MeCN—H2O), affording 20 mg (10%) of the title compound 4 as a white solid after lyophilization: 1H (400 MHz, DMSO-d6) δ 8.33 (s, 1H), 6.86 (br s, 2H), 6.09 (br s, 1H), 5.19 (br s, 1H), 4.88 (br s, 1H), 4.55 (t, J=5.87, 1H), 3.97 (br s, 1H), 3.76-3.81 (m, 1H), 3.61 (br s, 2H), 1.04 (s, 3H); [M+H]+ m/z 315. Analysis calc'd for C11H14N4O5S.H2O: C, 39.75; H, 4.85; N, 16.86; S, 9.65.

Workup

  1. concentrationconcentrated
  2. customsubmitted to HPLC purification (MeCN—H2O)

Sources & evidence

ORD record
ord-4b837d8121e84255b648b24c42a2d04c
Source dataset
uspto-grants-2012_01
Patent number
US08097718B2

Reaction notes

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