1,5-Diazabicyclo(5,4,0)undec-5-ene → HCID 86737859, compound
Reaction equation
[C:1]([NH:4]/[CH:5]=[CH:6]/[S:7][C:8]1[CH2:14][C@H:13]2[N:10]([C:11](=[O:24])[C@H:12]2[C@@H:15](OS(OCC)(=O)=O)[CH3:16])[C:9]=1[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])(=[O:3])[CH3:2].[C:35]([NH:38]/[CH:39]=[CH:40]/[S:41][C:42]1[CH2:48][C@H:47]2[N:44]([C:45](=[O:56])[C@H:46]2[C@@H:49](OS([O-])(=O)=O)[CH3:50])[C:43]=1[C:57]([O:59][CH2:60][C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)=[O:58])(=[O:37])[CH3:36].[Na+].N12CCCCC1C=NCCC2>>[C:1]([NH:4]/[CH:5]=[CH:6]/[S:7][C:8]1[CH2:14][C@H:13]2[N:10]([C:11](=[O:24])/[C:12]/2=[CH:15]/[CH3:16])[C:9]=1[C:25]([O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:26])(=[O:3])[CH3:2].[C:35]([NH:38]/[CH:39]=[CH:40]/[S:41][C:42]1[CH2:48][C@H:47]2[N:44]([C:45](=[O:56])/[C:46]/2=[CH:49]\[CH3:50])[C:43]=1[C:57]([O:59][CH2:60][C:61]1[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=1)=[O:58])(=[O:37])[CH3:36]Participants
Procedure
Benzyl (5R,6R)-3-[(E)-2-acetamidoethenylthio]-6-[(S)-1-ethoxysulphonyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (e24) prepared from sodium (5R,6R)-3-[(E)-2-acetamidoethenylthio]-6-[(S)-1-sulphonatooxyethyl]-7-oxo-2-benzyloxycarbonyl-1-azabicyclo[3.2.0]hept-2-ene (e23) (100 mg) as described in Example 13 was treated with 1,5-diazabicyclo[5.4.0]-undec-5-ene (35 mg) in an analogous manner to that described in Example 19 to give benzyl (5R,6E)-3-[(E)-2-acetamidoethenylthio]-6-ethylidene-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate and benzyl (5R,6Z)-3-[(E)-2-acetamidoethenylthio]-6-ethylidene-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (e45 and e37) (30 mg). The n.m.r. spectrum [CDCl3 +(CD3)2SO]indicated that the ethylidene group was largely in the E-form (e45) but that some Z-form (e37) was also present.
Sources & evidence
- ORD record
- ord-0e232ad242a249b089cdaf365f173d5e
- Source dataset
- uspto-grants-1981_07
- Patent number
- US04278686
Reaction notes
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