Hydrochloric Acid → HCID 59134416, compound

HRID 1993473Notes

Reaction equation

HRID 1993473 reaction equation
[NH2:1][C@H:2]1[C:7]2[CH:8]=[C:9]([NH2:13])[C:10]([NH2:12])=[CH:11][C:6]=2[O:5][C:4]([CH3:15])([CH3:14])[C@@H:3]1[OH:16].[CH:17]([CH:19]=O)=O.Cl>C(O)C>[NH2:1][C@H:2]1[C:7]2[CH:8]=[C:9]3[C:10]([N:12]=[CH:17][CH:19]=[N:13]3)=[CH:11][C:6]=2[O:5][C:4]([CH3:14])([CH3:15])[C@@H:3]1[OH:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7860GlyoxalHCID 68425553HCID 68425553, compound

Product 1

HCID 59134416HCID 59134416, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (3R*,4S*)-4,6,7-triamino-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-3-ol (280 mg, 1.25 mmol) in ethanol (5.6 mL), 40% aqueous glyoxal solution (226 mg, 1.56 mmol) was added, and the resulting mixture was stirred at room temperature for 1 hour. Upon the completion of the reaction, 1 mol/L hydrochloric acid was added thereto, the resulting solution was washed with ethyl acetate, the resulting aqueous phase was adjusted to pH 14 with 1 mol/L aqueous sodium hydroxide solution. Then, the resulting solution was extracted with ethyl acetate, washed with saturated sodium chloride solution, and dried over magnesium sulfate and concentrated. The resulting mixture was purified by silica gel column (ethyl acetate/methanol=10/1) to obtain the aimed product (yield: 35%).

Workup

  1. additionwas added
  2. washthe resulting solution was washed with ethyl acetate
  3. extractionThen, the resulting solution was extracted with ethyl acetate
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe resulting mixture was purified by silica gel column (ethyl acetate/methanol=10/1)

Sources & evidence

ORD record
ord-888675fa084d45fd89415705c06e2226
Source dataset
uspto-grants-2010_01
Patent number
US07652008B2

Reaction notes

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