Sodium Iodide → HCID 131724903, compound

HRID 2183085Notes

Reaction equation

HRID 2183085 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)[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[CH2:65]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.[N+:67]([C:70]1[CH:77]=[C:76]([N+:78]([O-:80])=[O:79])[CH:75]=[CH:74][C:71]=1[CH:72]=O)([O-:69])=[O:68].[I-].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.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: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:41]4[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=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:65]=[CH:72][C:71]1[CH:74]=[CH:75][C:76]([N+:78]([O-:80])=[O:79])=[CH:77][C:70]=1[N+:67]([O-:69])=[O:68])=[O:16])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 6

HCID 5238Sodium IodideHCID 11776TriphenylphosphineHCID 682502,4-DinitrobenzaldehydeHCID 516892Sodium BicarbonateHCID 131724899HCID 131724899, compoundHCID 131724904HCID 131724904, compound

Product 1

HCID 131724903HCID 131724903, compoundYield 64.2%

Procedure

7-[2-tert-butoxycarbonylmethoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-chloromethyl-3-cephem-4-carboxylic acid benzhydryl ester (500 mg, 0.53 mmol), 2,4-dinitrobenzaldehyde (416 mg, 2.12 mmol), sodium iodide (79.4 mg, 0.53 mmol), triphenylphosphine (139 mg, 0.53 mmol) and sodium hydrogen carbonate (133.6 mg, 1.59 mmol) were used to conduct the procedure similar to that shown in (1) of Example 1 to obtain 350 mg (yield: 61%) of 7-[2-carboxymethoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-(2,4-dinitrostyryl)-3-cephem-4-carboxylic acid benzhydryl ester as yellow powder.

Sources & evidence

ORD record
ord-4ce50b19959e4ada9dc092e7a8e9116a
Source dataset
uspto-grants-2005_05
Patent number
US06897304B2

Reaction notes

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