Glyoxal → HCID 59134392, compound

HRID 1993472Notes

Reaction equation

HRID 1993472 reaction equation
[NH2:1][C:2]1[C:3]([NH2:24])=[CH:4][C:5]2[O:10][C:9]([CH3:12])([CH3:11])[C@H:8]([OH:13])[C@@H:7]([NH:14][CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:6]=2[CH:23]=1.[CH:25]([CH:27]=O)=O.C(OCC)(=O)C>C(O)C>[CH3:12][C:9]1([CH3:11])[O:10][C:5]2[CH:4]=[C:3]3[C:2](=[CH:23][C:6]=2[C@H:7]([NH:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:8]1[OH:13])[N:1]=[CH:27][CH:25]=[N:24]3

Participants

5

Reactant 3

HCID 7860GlyoxalHCID 8857Ethyl AcetateHCID 59430995HCID 59430995, compound

Product 1

HCID 59134392HCID 59134392, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (3R*,4S*)-6,7-diamino-3,4-dihydro-2,2-dimethyl-4-(2-phenylethylamino)-2H-benzopyran-3-ol (1.5 g, 4.58 mmol) in ethanol (30 mL), 40% aqueous glyoxal solution (997 mg, 6.87 mmol) was added, and the resulting mixture was stirred at room temperature for 30 minutes. Upon the completion of the reaction, ethyl acetate was added thereto, the resulting solution was washed with saturated aqueous sodium hydrogencarbonate solution and then with saturated sodium chloride solution, and then dried over magnesium sulfate and concentrated. The resulting mixture was purified by silica gel column (hexane/ethyl acetate=1/1) to obtain the aimed product (yield: 74%).

Workup

  1. additionwas added
  2. washthe resulting solution was washed with saturated aqueous sodium hydrogencarbonate solution
  3. dry with materialwith saturated sodium chloride solution, and then dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe resulting mixture was purified by silica gel column (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-b9f952187740427cb17bc45f946795c9
Source dataset
uspto-grants-2010_01
Patent number
US07652008B2

Reaction notes

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