Potassium Carbonate → HCID 11220995, compound

HRID 1509804Notes

Reaction equation

HRID 1509804 reaction equation
[CH2:1]([N:4]1[C:12]2[C:7](=[N:8][C:9]([NH2:13])=[N:10][CH:11]=2)[N:6]([C@@H:14]2[O:26][C@H:25]([CH2:27][O:28]C(=O)C)[C@@H:20]([O:21]C(=O)C)[C@H:15]2[O:16]C(=O)C)[C:5]1=[O:32])[CH:2]=[CH2:3].C([O-])([O-])=O.[K+].[K+]>CO>[CH2:1]([N:4]1[C:12]2[C:7](=[N:8][C:9]([NH2:13])=[N:10][CH:11]=2)[N:6]([C@@H:14]2[O:26][C@H:25]([CH2:27][OH:28])[C@@H:20]([OH:21])[C@H:15]2[OH:16])[C:5]1=[O:32])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 59598980HCID 59598980, compound

Product 1

HCID 11220995HCID 11220995, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 42 (0.13 g, 0.29 mmol) in methanol (4 mL) was added solid K2CO3 (0.024 g, 0.17 mmol) and the reaction stirred at ambient temperature for 18 h. To the cloudy mixture was added Amberlite CG-50 (0.5 g) and stirred till neutral and filtered. The filtrate was concentrated to give an off-white solid, which was washed with water and dried under high vacuum to give 93.5 mg of pure 43 in quantitative yield as an off white solid: 1H NMR (400 MHz, d6-DMSO) δ 7.88 (s, 1H), 6.33 (br s, 2H), 5.85 (m, 1H), 5.66 (d, J=6.0 Hz, 1H), 5.30 (d, J=5.6 Hz, 1H), 5.20 (s, 1H), 5.16 (d, J=8.4 Hz, 1H), 5.01 (d, J=4.8 Hz, 1H), 4.89 (q, J=5.6 Hz, 1H), 4.75 (br s, 1H), 4.35 (d, J=5.2 Hz, 2H), 4.10 (t, J=8.4 Hz, 1) 3.80 (q, J=3.6 Hz, 1H), 3.57 (m, 1H), 3.44 (m, 1H). MS (+)-ES [M+H]+ 324.1 m/z.

Workup

  1. additionTo the cloudy mixture was added Amberlite
  2. stirring(0.5 g) and stirred till neutral and
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customto give an off-white solid, which
  6. washwas washed with water
  7. customdried under high vacuum
  8. customto give 93.5 mg of pure 43 in quantitative yield as an off white solid

Sources & evidence

ORD record
ord-2016b23188c84674be910a8f646abac6
Source dataset
uspto-grants-2012_07
Patent number
US08211863B2

Reaction notes

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