4-Nitrobenzaldehyde → HCID 131724897, compound

HRID 2183081Notes

Reaction equation

HRID 2183081 reaction equation
[CH:1]([O:14][C:15]([C:17]1[N:22]2[C:23](=[O:66])[CH:24]([NH:25][C:26](=[O:65])[C:27](=[N:53][O:54][C:55]([CH3:64])([C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58])[CH3:56])[C:28]3[N:29]=[C:30]([NH:33][C:34]([C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[S:31][CH:32]=3)[C@H:21]2[S:20][CH2:19][C:18]=1[CH2:67]Cl)=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+:90]([C:93]1[CH:100]=[CH:99][C:96]([CH:97]=O)=[CH:95][CH:94]=1)([O-:92])=[O:91].C(=O)([O-])O.[Na+].NC1SC=C(C(=NOC(C(O)=O)(C)C)C(NC2C(=O)N3C(C(O)=O)=C(C=CC4C=CC([N+]([O-])=O)=CC=4[N+]([O-])=O)CS[C@H]23)=O)N=1>>[CH:1]([O:14][C:15]([C:17]1[N:22]2[C:23](=[O:66])[CH:24]([NH:25][C:26](=[O:65])[C:27](=[N:53][O:54][C:55]([CH3:64])([C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58])[CH3:56])[C:28]3[N:29]=[C:30]([NH:33][C:34]([C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[S:31][CH:32]=3)[C@H:21]2[S:20][CH2:19][C:18]=1[CH:67]=[CH:97][C:96]1[CH:99]=[CH:100][C:93]([N+:90]([O-:92])=[O:91])=[CH:94][CH:95]=1)=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 6

HCID 5414-NitrobenzaldehydeHCID 5238Sodium IodideHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 131724898HCID 131724898, compoundHCID 131724899HCID 131724899, compound

Product 1

HCID 131724897HCID 131724897, compoundYield 66.5%

Procedure

7-[2-(1-methyl-1-tert-butoxycarbonylethoxyimino)-2-(2-tritylaminothiazol-4-yl)acetamido]-3-chloromethyl-3-cephem-4-carboxylic acid benzhydryl ester (775 mg, 0.8 mmol), sodium iodide (120 mg, 0.8 mmol), triphenylphosphine (210 mg, 0.8 mmol), 4-nitrobenzaldehyde (483 mg, 3.2 mmol) and sodium hydrogen carbonate (200 mg, 2.4 mmol) were used to conduct the procedure similar to that shown in (1) of Example 1 to obtain 568 mg (yield: 66%) of 7-[2-(1-methyl-1-tert-butoxycarbonylethoxyimino)-2-(2-tritylaminothiazol-4-yl)acetamido]-3-(4-nitrostyryl)-3-cephem-4-carboxylic acid benzhydryl ester as yellow powder.

Sources & evidence

ORD record
ord-d646fec045754c5a84f3dee3aeb39eed
Source dataset
uspto-grants-2005_05
Patent number
US06897304B2

Reaction notes

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