Reaction equation
[CH3:1][O:2][C:3]([CH:5]1[C:9](=O)[CH2:8][S:7][CH2:6]1)=[O:4].Cl.[NH2:12][OH:13]>>[CH3:1][O:2][C:3]([CH:5]1[C:9](=[N:12][OH:13])[CH2:8][S:7][CH2:6]1)=[O:4]Participants
3
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-d591ede4f62046339552f194d440be9b
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07365200B2
Linked notes
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