2,2,2-Trichloroethyl 2-methyl-2,3-methylene-6-[2-(2-thienyl)acetamido]penam-3-carboxylate → 2-Methyl-2,3-methylene-6-[2-(2-thienyl)acetamido]penam-3-carboxylic acid
Reaction equation
[CH3:1][C:2]12[CH2:15][C:6]1([C:7]([O:9]CC(Cl)(Cl)Cl)=[O:8])[N:5]1[C:16](=[O:27])[CH:17]([NH:18][C:19](=[O:26])[CH2:20][C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)[C@H:4]1[S:3]2>CN(C)C=O.C(O)(=O)C.[Zn]>[CH3:1][C:2]12[CH2:15][C:6]1([C:7]([OH:9])=[O:8])[N:5]1[C:16](=[O:27])[CH:17]([NH:18][C:19](=[O:26])[CH2:20][C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)[C@H:4]1[S:3]2Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of 2,2,2-trichloroethyl 2-methyl-2,3-methylene-6-[2-(2-thienyl)acetamido]penam-3-carboxylate (1.4 g.) in a mixture of dimethylformamide (7.5 ml.) and acetic acid (1.75 ml.) was added zinc powder (1.8 g.) unde ice cooling, and the mixture was stirred for 1 hour. After the reaction, the reaction mixture was post-treated in the similar manner as described in Example 1 to give 2-methyl-2,3-methylene-6-[2-(2-thienyl)acetamido]penam-3-carboxylic acid (0.8 g.), mp 106° to 108°C (dec.) Infrared Absorption Spectrum (Nujol): 3350, 1765, 1720 cm-1
Workup
- customAfter the reaction
- additionthe reaction mixture was post-treated in the similar manner
Sources & evidence
- ORD record
- ord-490e690f924847d88fc15d7417efcbfd
- Source dataset
- uspto-grants-1976_10
- Patent number
- US03984397
Reaction notes
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