Reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6](NCC(O)=O)=[CH:5][CH:4]=1.ClC([O:17][CH2:18][CH:19](C)C)=O.[C:22]([O:28][CH2:29][O:30][C:31]([C:33]1[N:34]2[CH:37]([S:38][CH2:39][C:40]=1[CH2:41][O:42][C:43](=[O:45])[CH3:44])[CH:36]([NH2:46])[C:35]2=[O:47])=[O:32])(=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24].C([N:50](CC)CC)C>>[C:22]([O:28][CH2:29][O:30][C:31]([C:33]1[N:34]2[CH:37]([S:38][CH2:39][C:40]=1[CH2:41][O:42][C:43](=[O:45])[CH3:44])[CH:36]([NH:46][C:18](=[O:17])[CH:19]([C:6]1[CH:5]=[CH:4][C:3]([CH2:2][Cl:1])=[CH:8][CH:7]=1)[NH2:50])[C:35]2=[O:47])=[O:32])(=[O:27])[C:23]([CH3:25])([CH3:26])[CH3:24]Participants
5
Reactant 4
Product 1
Procedure
p-Chloromethylphenylglycine wherein the amino group is protected with tert-butoxycarbonyl is treated with isobutyl chloroformate in the presenceof triethylamine. The thus obtained mixed anhydride is reacted with 3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid pivalyloxymethyl ester at 0° C. for about 4 hours. The resulting product is isolated, and the amine protecting group is removed by acid hydrolysis by treating the product with difluoroacetic acid for 5 minutes at room temperature to give 3-[(acetyloxy)methyl]-7-[[2-[4-(chloromethyl)phenyl]-2-aminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid pivalyloxymethyl ester.
Workup
- customThe thus obtained
- customThe resulting product is isolated
- customthe amine protecting group is removed by acid hydrolysis
- additionby treating the product with difluoroacetic acid for 5 minutes at room temperature
Sources & evidence
- ORD record
- ord-0a9da20f39f24e82b91c79db8ab4c1b8
- Source dataset
- uspto-grants-1977_05
- Patent number
- US04026887
Linked notes
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