Ethanolamine → 3-Benzyloxy-1-carboxymethyl-3-hydroxy-2-methylpyrid-4-one

HRID 1906184Notes

Reaction equation

HRID 1906184 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12]O[C:10]=1[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O:24]C1C(=O)C=COC=1C)C1C=CC=CC=1.C(N1C=CC(=O)C(O)=C1C)(=O)C.[NH2:45][CH2:46][C:47]([OH:49])=[O:48].OCCN>>[CH2:1]([O:8][C:9]1([OH:24])[C:14](=[O:15])[CH:13]=[CH:12][N:45]([CH2:46][C:47]([OH:49])=[O:48])[CH:10]1[CH3:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 700EthanolamineHCID 750GlycineHCID 14901193-Benzyloxy-2-methyl-4-pyroneHCID 867413491-acetyl-3-hydroxy-2-methylpyrid-4-one 3-Benzyloxy-2-methyl-4-pyrone

Product 1

HCID 571528933-Benzyloxy-1-carboxymethyl-3-hydroxy-2-methylpyrid-4-one

Procedure

3-Benzyloxy-2-methyl-4-pyrone, prepared as described under (J), is reacted with glycine under substantially similar conditions to those described under (K) for reaction with 2-hydroxyethylamine to give 3-benzyloxy-1-carboxymethyl-3-hydroxy-2-methylpyrid-4-one, which is deprotected using the procedure described under (I) to give 1-carboxymethyl-3-hydroxy-2-methylpyrid-4-one as white crystals, m.p. >230° C.; δmax (nujol) 1625, 1645 cm-1 ; δ(d6DMSO) 1.9 (s, 3H), 4.3 (s. 2H), 5.9 (d, 1H), 7.35 (d, 1H).

Sources & evidence

ORD record
ord-e73c6f6eaf4745b7b22fb4bb5611577b
Source dataset
uspto-grants-1987_03
Patent number
US04650793

Reaction notes

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