4-Nitrobenzaldehyde → HCID 131724901, compound

HRID 2183083Notes

Reaction equation

HRID 2183083 reaction equation
[CH:1]([O:14][C:15]([C:17]1[N:22]2[C:23](=[O:57])[CH:24]([NH:25][C:26](=[O:56])[C:27](=[N:53][O:54][CH3:55])[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[CH2:58]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+:81]([C:84]1[CH:91]=[CH:90][C:87]([CH:88]=O)=[CH:86][CH:85]=1)([O-:83])=[O:82].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:57])[CH:24]([NH:25][C:26](=[O:56])[C:27](=[N:53][O:54][CH3:55])[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:58]=[CH:88][C:87]1[CH:90]=[CH:91][C:84]([N+:81]([O-:83])=[O:82])=[CH:85][CH:86]=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 131715761HCID 131715761, compoundHCID 131724899HCID 131724899, compound

Product 1

HCID 131724901HCID 131724901, compoundYield 55%

Procedure

7-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-chloromethyl-3-cephem-4-carboxylic acid benzhydryl ester (395 mg, 0.47 mmol), sodium iodide (70 mg, 0.47 mmol), triphenylphosphine (123 mg, 0.47 mmol), 4-nitrobenzaldehyde (284 mg, 1.88 mmol) and sodium hydrogen carbonate (120 mg, 1.4 mmol) were used to conduct the procedure similar to that shown in (1) of Example 1 to obtain 242 mg (yield: 55%) of 7-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-(4-nitrostyryl)-3-cephem-4-carboxylic acid benzhydryl ester as yellow powder.

Sources & evidence

ORD record
ord-91565fffdc72466a88d3e662ff12af29
Source dataset
uspto-grants-2005_05
Patent number
US06897304B2

Reaction notes

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