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

HRID 355288Notes

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.[NH2:17][CH2:18][C:19]([OH:21])=[O:20].[OH:22]CCN>>[CH2:1]([O:8][C:9]1([OH:22])[C:14](=[O:15])[CH:13]=[CH:12][N:17]([CH2:18][C:19]([OH:21])=[O:20])[CH:10]1[CH3:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 700Ethanolamine

HCID 750Glycine

HCID 14901193-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 Example 10, is reacted with glycine under substantially similar conditions to those described under Example 11 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 Example 11 to give 1-carboxymethyl-3-hydroxy-2-methylpyrid-4-one as white crystals, m.p >230° C.; νmax (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-09cd29df07fe486da13d68f20ccd69a5
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE035948

Reaction notes

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