4-Nitrobenzaldehyde → HCID 131724906, compound

HRID 2183087Notes

Reaction equation

HRID 2183087 reaction equation
[CH:1]([O:14][C:15]([C:17]1[N:22]2[C:23](=[O:64])[CH:24]([NH:25][C:26](=[O:63])[C:27](=[N:53][O:54][CH2:55][C:56]([O:58]C(C)(C)C)=[O:57])[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)C4C=CC=CC=4)[S:31][CH:32]=3)[C@H:21]2[S:20][CH2:19][C:18]=1[CH2:65]Cl)=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)C1C=CC=CC=1.[I-].[Na+].[C:69]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1.[N+:88]([C:91]1[CH:98]=[CH:97][C:94]([CH:95]=O)=[CH:93][CH:92]=1)([O-:90])=[O:89].C(=O)([O-])O.[Na+].NC1SC=C(C(=NOC(C(O)=O)(C)C)C(NC2C(=O)N3C(C(O)=O)=C(C=C[C:123]4[CH:128]=[CH:127][C:126]([N+]([O-])=O)=[CH:125][C:124]=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:64])[CH:24]([NH:25][C:26](=[O:63])[C:27](=[N:53][O:54][CH2:55][C:56]([OH:58])=[O:57])[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:123]4[CH:128]=[CH:127][CH:126]=[CH:125][CH:124]=4)[C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[S:31][CH:32]=3)[C@H:21]2[S:20][CH2:19][C:18]=1[CH:65]=[CH:95][C:94]1[CH:97]=[CH:98][C:91]([N+:88]([O-:90])=[O:89])=[CH:92][CH:93]=1)=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1

Participants

7

Reactant 6

HCID 5414-NitrobenzaldehydeHCID 5238Sodium IodideHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 131724899HCID 131724899, compoundHCID 131724904HCID 131724904, compound

Product 1

HCID 131724906HCID 131724906, compoundYield 50%

Procedure

7-[2-tert-butoxycarbonylmethoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-chloromethyl-3-cephem-4-carboxylic acid benzhydryl ester (470 mg, 0.5 mmol), sodium iodide (75 mg, 0.5 mmol), triphenylphosphine (131 mg, 0.5 mmol), 4-nitrobenzaldehyde (302 mg, 2 mmol) and sodium hydrogen carbonate (126 mg, 1.5 mmol) were used to conduct the procedure similar to that shown in (1) of Example 1 to obtain 260 mg (yield: 50%) of 7-[2-carboxymethoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-(4-nitrostyryl)-3-cephem-4-carboxylic acid benzhydryl ester as yellow powder.

Sources & evidence

ORD record
ord-171e8d87ca81409d90f342a41a1db9a5
Source dataset
uspto-grants-2005_05
Patent number
US06897304B2

Reaction notes

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