Chloride → Methyl 2-(chloromethyl)oxazole-4-carboxylate

HRID 864497Notes

Reaction equation

HRID 864497 reaction equation
[CH3:1][O:2][C:3](=[O:8])[C@H:4]([CH2:6][OH:7])[NH2:5].C(O[CH2:14][C:15](O)=O)(C)(C)C.[Cl-:18]>>[Cl:18][CH2:14][C:15]1[O:7][CH:6]=[C:4]([C:3]([O:2][CH3:1])=[O:8])[N:5]=1

Participants

4

Reactant 3

HCID 312ChlorideHCID 2723731(S)-methyl 2-amino-3-hydroxypropanoateHCID 27609982-(Tert-butoxy)acetic acid

Product 1

HCID 2763199Methyl 2-(chloromethyl)oxazole-4-carboxylate

Procedure

Oxazoles and Oxazolines Yokokawa (Synthetic Lett., 1992, 2, 153) has recently described the preparation and cyclization of N-acylserine ester derivatives to give 2-substituted-4,5-dihydrooxazole-4-carboxylate esters which, after oxidation, give the corresponding 2-substituted-oxazole-4-carboxylate esters. By inference, N-acylation of serine methyl ester with t-butoxyacetic acid, followed by cyclization, oxidation, deprotection and conversion to the chloride by standard methods should give methyl 2-(chloromethyl)oxazole-4-carboxylate, as outlined in Scheme XX below. Eliminiation of the oxidation step will give the corresponding oxazoline. ##STR52##

Sources & evidence

ORD record
ord-34f5e357bf2c4c86a1f98d900a87e768
Source dataset
uspto-grants-1996_10
Patent number
US05563158

Reaction notes

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