3-Hydroxybenzaldehyde → HCID 28432204, compound

HRID 1770513Notes

Reaction equation

HRID 1770513 reaction equation
[CH3:1][O:2][C:3](=[O:6])[CH2:4][NH2:5].[OH:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=O.C(O)(=O)C.C([BH3-])#N.[Na+].C1COCC1>C1COCC1.CO>[OH:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11][NH:5][CH2:4][C:3]([O:2][CH3:1])=[O:6]

Participants

7

Reactant 5

HCID 1013-HydroxybenzaldehydeHCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 69221Glycine methyl esterHCID 5003444Sodium cyanoborohydride

Product 1

HCID 28432204HCID 28432204, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Glycine methyl ester (500 mg, 4 mmol) and 3-hydroxybenzaldehyde (480 mg, 4 mmol) were dissolved in 5 mL THF/Methanol (1:1). Acetic acid (240 mg, 4 mmol), and 1M sodium cyanoborohydride in THF (4.8 mL, 4.8 mmol) were slowly added into the reaction. The reaction was irradiated in the microwave reactor at 85° C. for 15 minutes, cooled to room temperature and the salts were removed by filtration. The clear solution was concentrated and the residue was purified by reversed phase HPLC (10 to 95% Acetonitrile in H2O:25 minute gradient) to give the title compound as a clear gel. Yield 45%. MS M+H calculated 196.1. Found 196.1.

Workup

  1. customThe reaction was irradiated in the microwave reactor at 85° C. for 15 minutes
  2. customthe salts were removed by filtration
  3. concentrationThe clear solution was concentrated
  4. customthe residue was purified by reversed phase HPLC (10 to 95% Acetonitrile in H2O:25 minute gradient)

Sources & evidence

ORD record
ord-0b1ed326552f49cd9fce5f523054378c
Source dataset
uspto-grants-2016_02
Patent number
US09247759B2

Reaction notes

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