108607-02-9 Purity
95%
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Specification
The deuterium-labeled internal standard drug cefuroxime was synthesized using methoxy-d3-amine hydrochloride through a five-step procedure, which can be used in a wide range of pharmacological studies of cefuroxime.
Synthesis procedure of cefuroxime-d1
· A 66% yield of d3-(2Z)-2-(2-Furyl)-2-(methoxyimino)acetic acid 3 was obtained by reacting 2-(2-furyl)-2-oxoacetic acid 2 with methoxyl-d3-amine hydrochloride in ethanol under reflux conditions for 6 hours.
· The resulting compound 3 was then converted to acid chloride 4 using oxalyl chloride in the presence of DMF, and without purification, acid chloride 4 was used in the acylation of 7-ACA in dichloromethane with DIPEA, yielding amide 5 in 67% yield.
· Hydrolysis of the ester group in 5 was achieved by treatment with NaOH at temperatures below -20°C for approximately 5 hours.
· Further experimentation showed that acid 6 could undergo intramolecular esterification to form lactone 7 when neutralization was carried out at room temperature. By reducing the workup temperature to below -20°C, a 73% yield of hydroxy acid 6 was obtained, thus improving the overall efficiency of the reaction.
The molecular formula is CH6ClNO.
The synonyms are Methoxyl-d3-amine Hydrochloride, O-(Trideuteriomethyl)hydroxylamine;hydrochloride, Methoxyamine-d3 (Hydrochloride), and Methoxyl-d3-amine HCl.
The molecular weight is 86.53 g/mol.
The parent compound is Methoxy-d3-amine.
Yes, Methoxyl-d3-amine Hydrochloride contains Methoxy-d3-amine and Hydrochloric Acid as component compounds.
Methoxyl-d3-amine Hydrochloride was created on February 1, 2011.
Methoxyl-d3-amine Hydrochloride was last modified on October 21, 2023.
The IUPAC Name is O-(trideuteriomethyl)hydroxylamine;hydrochloride.
The InChIKey is XNXVOSBNFZWHBV-NIIDSAIPSA-N.
The CAS number is 110220-55-8.