Aminoacetaldehyde dimethyl acetal → HCID 46239167, compound

HRID 406921Notes

Reaction equation

HRID 406921 reaction equation
[O:1]=[C:2]1[CH:7]=[CH:6]O[C:4]([C:8]([OH:10])=[O:9])=[C:3]1[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH3:19][O:20][CH:21]([O:24][CH3:25])[CH2:22][NH2:23]>C(O)C>[CH3:19][O:20][CH:21]([O:24][CH3:25])[CH2:22][N:23]1[CH:6]=[CH:7][C:2](=[O:1])[C:3]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[C:4]1[C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 217925463-(Benzyloxy)-4-oxo-4h-pyran-2-carboxylic acid

Product 1

HCID 46239167HCID 46239167, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a flask (1 L) charged with 500 mL of anhydrous ethanol was added 49.2 g (0.2 mol) of 4-oxo-3-[(phenylmethyl)oxy]-4H-pyran-2-carboxylic acid 5. The suspension was slowly heated to 55-60° C. before addition of 2-amino-acetaldehyde-dimethylacetal (84.1 g, 0.8 mole). The reaction was then brought up to 65° C. and further stirred for 18 hours. The solvent was removed under reduced pressure to produce 1-[2,2-Bis(methyloxy)ethyl]-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylic acid 22 (crude) as brown oil, which was used for the next step directly.

Workup

  1. customwas then brought up to 65° C.
  2. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6a8b8a78bd7a4deda05a7fa00780e83f
Source dataset
uspto-grants-2014_06
Patent number
US08754214B2

Reaction notes

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