m-Chloroperbenzoic acid → HCID 69732331, compound

HRID 1071822Notes

Reaction equation

HRID 1071822 reaction equation
S1C=CC=C1N([C@@H]1C(=O)N2C(C(OC(C3C=CC=CC=3)C3C=CC=CC=3)=O)=C(CSC3N(C)N=NN=3)CS[C@H]12)C(C)=O.S1C=CC=C1N([C@@H:52]1[C:82](=[O:83])[N:54]2[CH:55](C(OC(C3C=CC=CC=3)C3C=CC=CC=3)=S)[C:56]([C:60]3[N:64]([CH3:65])[N:63]=[N:62][N:61]=3)(C)[CH2:57][S:58][C@H:53]12)C(C)=O.CSC1(CCl)CN2C(=O)C[C@H]2SC1.ClC1C=CC=C(C(OO)=O)C=1>>[CH3:65][N:64]1[C:60]([C:56]2[CH2:57][S:58][C@@H:53]3[CH2:52][C:82](=[O:83])[N:54]3[CH:55]=2)=[N:61][N:62]=[N:63]1

Participants

5

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 69730436HCID 69730436, compoundHCID 131724998HCID 131724998, compoundHCID 131724999HCID 131724999, compound2×

Product 1

HCID 69732331HCID 69732331, compound

Procedure

Finally, T. Aoki et al. (Tetrahedron 1983, 34/15, 2515-2556—in particular pages 2520-2525) disclose the synthesis of diphenylmethyl 7β-(2-thienylacetamino)-3-(1-methyl-1H-tetrazol-5-yl)thiometyl-3-cephem-4-carboxylate, which involves the preparation of diphenylmethyl 7β-(2-thienylacetamino)-3-(l-methyl-1H-tetrazol-5-yl)-3-methylthiocepham-4-carboxylate via the corresponding 3-methylthio-3-chloromethylcepham analog and the reaction of said diphenylmethyl 7β-(2-thienylacetamino)-3-(1-methyl-1H-tetrazol-5-yl)-3-methylthiocepham-4-carboxylate with m-chloroperbenzoic acid in order to remove methylmercaptan and form a 3-(1-methyl-1H-tetrazol-5-yl)-3-cephem structure via the corresponding 1-oxide. However, the method described by Aoki et al. is not transposable to the preparation of third-generation-cefalosporins because the reactants employed affect the amino group which is present on the thiazole ring and is sensitive thereto.

Workup

  1. customto remove methylmercaptan

Sources & evidence

ORD record
ord-b4955aac6eb84df9ab933ddc1fcba28f
Source dataset
uspto-grants-2005_06
Patent number
US06906187B2

Reaction notes

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