Chlorotrimethylsilane → HCID 24880120, compound

HRID 529250Notes

Reaction equation

HRID 529250 reaction equation
[OH:1][C:2]1[C:10]2[O:9][C:8]([NH:11][CH2:12][C:13]([OH:15])=[O:14])=[C:7]([C:16](=[O:29])[C:17]3[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=3)[C:6]=2[CH:5]=[CH:4][C:3]=1[O:30][CH3:31].[CH3:32][Si](Cl)(C)C>CO>[CH3:32][O:14][C:13](=[O:15])[CH2:12][NH:11][C:8]1[O:9][C:10]2[C:2]([OH:1])=[C:3]([O:30][CH3:31])[CH:4]=[CH:5][C:6]=2[C:7]=1[C:16](=[O:29])[C:17]1[CH:18]=[C:19]([O:27][CH3:28])[C:20]([O:25][CH3:26])=[C:21]([O:23][CH3:24])[CH:22]=1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 24880119HCID 24880119, compound

Product 1

HCID 24880120HCID 24880120, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[7-hydroxy-6-methoxy-3-(3,4,5-trimethoxy-benzoyl)-benzofuran-2-ylamino]acetic acid (30 mg, 0.07 mmol) was dissolved in dry methanol (5 mL) and trimethylsilyl chloride (100 μL) was added to it. The reaction was stirred at room temperature for 6 hours (monitored by tlc). Solvent was distilled under vacuum and the crude was purified over silica gel plate to afford the title compound as yellow solid (23 mg, 79%); 1H NMR (300 MHz, CDCl3) δ 9.11 (b, 1H, NH), 6.97 (s, 2H, benzoyl Hs), 6.62 (d, 1H, J=8.56 Hz), 6.51 (d, 1H, J=8.49 Hz), 4.42 (d, 1H, J=6.09 Hz), 3.91 (s, 3H, OMe), 3.86 (s, 3H, OMe), 3.84 (s, 6H, 2×OMe), 3.81 (s, 3H, OMe).

Workup

  1. distillationSolvent was distilled under vacuum
  2. customthe crude was purified over silica gel plate

Sources & evidence

ORD record
ord-c4c85db2652d43bfa476b9941adf9e92
Source dataset
uspto-grants-2016_05
Patent number
US09346842B2

Reaction notes

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