3-Hydroxybenzaldehyde → HCID 28432204, compound

HRID 548112Notes

Reaction equation

HRID 548112 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-fcf56d16ee1e454eb8e4a89d3448be7b
Source dataset
uspto-grants-2011_05
Patent number
US07939671B2

Reaction notes

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