Methyl Acrylate → Propanoic acid, 3-((2-methoxy-2-oxoethyl)thio)-, methyl ester
Reaction equation
[CH3:1][O:2][C:3]([C:5]1C(N)=CS[CH:6]=1)=[O:4].[C:11]([O:15][CH3:16])(=[O:14])[CH2:12][SH:13].C(OC)(=O)C=C>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][S:13][CH2:12][C:11]([O:15][CH3:16])=[O:14]Participants
4
Procedure
Compounds of structure (II) were prepared by using 4-amino-thiophene-3-carboxylic acid methyl ester, as depicted by formula (21), as a starting material. To make this compound, methyl thioglycolate was reacted with methyl acrylate to yield intermediate 3-methoxycarbonylmethylsulfanyl-propionic acid methyl ester, depicted by formula (18), which was cyclized to 4-oxo-tetrahydro-thiophene-3-carboxylic acid methyl ester, depicted by formula (19). This intermediate was reacted with hydroxylamine hydrochloride to yield 4-hydroxyimino-tetrahydro-thiophene-3-carboxylic acid methyl ester, depicted by formula (20), which yielded 4-amino-thiophene-3-carboxylic acid methyl ester hydrochloride, depicted by formula (21), as shown in Scheme 10.
Sources & evidence
- ORD record
- ord-672138ae87dc4fb08f0eb4628b87430f
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07365200B2
Reaction notes
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