Glycine → HCID 24880119, compound

HRID 529249Notes

Reaction equation

HRID 529249 reaction equation
Br[C:2]1[O:3][C:4]2[C:24]([O:25]C(=O)C)=[C:23]([O:29][CH3:30])[CH:22]=[CH:21][C:5]=2[C:6]=1[C:7](=[O:20])[C:8]1[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[C:10]([O:18][CH3:19])[CH:9]=1.[NH2:31][CH2:32][C:33]([OH:35])=[O:34].C(=O)([O-])[O-].[K+].[K+]>CC#N.O>[OH:25][C:24]1[C:4]2[O:3][C:2]([NH:31][CH2:32][C:33]([OH:35])=[O:34])=[C:6]([C:7](=[O:20])[C:8]3[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[C:10]([O:18][CH3:19])[CH:9]=3)[C:5]=2[CH:21]=[CH:22][C:23]=1[O:29][CH3:30]

Participants

5

Reactant 3

HCID 750GlycineHCID 11430Potassium CarbonateHCID 247865602-Bromo-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxybenzofuran

Product 1

HCID 24880119HCID 24880119, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

A mixture of 2-bromo-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxy-benzofuran (50 mg, 0.10 mmol), glycine (18 mg, 0.29 mmol) and potassium carbonate (29 mg, 0.21 mmol) in a mixture of MeCN/water 80:20 (5 mL) was refluxed for six hours. Solvent was distilled and the residue was taken in water:dichloromethane 1:2 (30 mL) and stirred for 20 minutes. Aqueous layer was separated, washed with dichloromethane (20 mL) and acidified with 2 drops of concentrated HCl and was diluted with dichloromethane (50 mL) and was stirred for 30 minutes. The organic layer was separated and dried over magnesium sulfate and solvent was distilled to afford the title compound as yellow powder (23 mg, 51%); 1H NMR (300 MHz, Acetone d6) δ 9.09 (b, 1H, NH), 6.97 (s, 2H, benzoyl Hs), 6.74 (d, 1H, J=8.53 Hz), 6.45 (d, 1H, J=8.48 Hz), 4.48 (d, 2H, J=4.28 Hz), 3.82 (s, 6H, 2×OMe), 3.79 (s, 3H, OMe), 3.78 (s, 3H, OMe).

Workup

  1. temperaturewas refluxed for six hours
  2. distillationSolvent was distilled
  3. customAqueous layer was separated
  4. washwashed with dichloromethane (20 mL)
  5. additionwas diluted with dichloromethane (50 mL)
  6. stirringwas stirred for 30 minutes
  7. customThe organic layer was separated
  8. dry with materialdried over magnesium sulfate and solvent
  9. distillationwas distilled

Sources & evidence

ORD record
ord-c450d82f22ab43daba7d71ce6e837652
Source dataset
uspto-grants-2016_05
Patent number
US09346842B2

Reaction notes

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