HCID 70586926, compound → HCID 70588450, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH:5]=[C:6]([NH:8][CH:9]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([CH2:20][S:21][CH:22]=NN)[CH:14]=1)[C:10]([OH:12])=[O:11])[CH3:7])[CH3:2].C(OC(=O)C=C(NC(C1C=CC(O)=C(CSC2NCCN=2)C=1)C(O)=O)C)C>>[CH2:1]([O:3][C:4](=[O:25])[CH:5]=[C:6]([NH:8][CH:9]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([CH2:20][S:21][CH3:22])[CH:14]=1)[C:10]([OH:12])=[O:11])[CH3:7])[CH3:2]Participants
Procedure
In like manner and using the appropriate quantities of reagents, substitution of α-(3-ethoxy-1-methyl-3-oxo-1-propen-1-yl)amino-3-[[(aminoiminomethyl)thio]methyl]-4-hydroxybenzeneacetic acid; α-(3-ethoxy-1-methyl-3-oxo-1-propen-1-yl)amino-3-[[(4,5-dihydro-1H-imidazol-2-yl)-thio]methyl]-4-hydroxybenzeneacetic acid; or α-(3-ethoxy-1-methyl-3-oxo-1-propen-1-yl)amino-4-hydroxy-3-[(methylthio)methyl]benzeneacetic acid in place of α-(3-ethoxy-1-methyl-3-oxo-1-propen-1-yl)amino-3-(azidomethyl)-4-hydroxybenzeneacetic acid gives the following respective compounds: 6-[[Amino[3-[[(aminoiminomethyl)thio]methyl]-4-hydroxyphenyl]acetyl]amino]3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 6-[[amino-3-[[[(4,5-dihydro-1H-imidazol-2-yl)thio]methyl]-4-hydroxyphenyl]acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; and 6-[[amino[4-hydroxy-3-[(methylthio)methyl]phenyl]acetyl]-amino]-3,3-dimethyl-7-oxo-5-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid.
Sources & evidence
- ORD record
- ord-d2cabdd688484dd3b75004c5be45dc01
- Source dataset
- uspto-grants-1980_04
- Patent number
- US04197240
Reaction notes
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