Acetic Acid → HCID 59128696, compound

HRID 1991104Notes

Reaction equation

HRID 1991104 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[C:15]3[C:10](=[N:11][CH:12]=[C:13](B4OC(C)(C)C(C)(C)O4)[CH:14]=3)[N:9]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[CH:8]=2)[CH:4]=[N:3]1.C(O)(=[O:35])C.OO>O>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[C:15]3[C:10](=[N:11][CH:12]=[C:13]([OH:35])[CH:14]=3)[N:9]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:31])([CH3:30])[CH3:32])[CH:8]=2)[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 59128702HCID 59128702, compound

Product 1

HCID 59128696HCID 59128696, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 25 (1.00 g, 2.20 mmol), glacial acetic acid (5.0 mL), H2O (5.0 mL) and 30% aq. H2O2 (370 μL, 3.30 mmol) were stirred for 8 h and partitioned between AcOEt/brine. The layers were separated, the aqueous phase extracted with more AcOEt and the combined organic extracts dried (MgSO4) and concentrated to give 27 as a creamy white solid (731 mg, 96%); 1H NMR (400 MHz, CDCl3) δ-0.058 (s, 9H), 0.92 (t, J=8.3 Hz, 2H), 3.58 (t, J=8.3 Hz, 2H), 4.01 (s, 3H), 2.01 (s, 2H), 7.37 (s, 1H), 7.56 (s, 1H), 7.66 (d, J=2.3 Hz, 1H), 7.95 (s, 1H), 8.17 (d, J=2.2 Hz, 1H), 9.00-9.60 (bs, OH).

Workup

  1. custompartitioned between AcOEt/brine
  2. customThe layers were separated
  3. extractionthe aqueous phase extracted with more AcOEt
  4. dry with materialthe combined organic extracts dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-659cfe04c5b64073913294b535fe2825
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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