Imidazole → HCID 70455674, compound

HRID 2290236Notes

Reaction equation

[CH2:1]([O:8][C:9]([C@@H:11]1[N:15]2[C:16](=[O:21])[C@@H:17]([C@H:18]([OH:20])[CH3:19])[C@H:14]2[S:13](=[O:23])(=[O:22])[C:12]1([CH3:25])[CH3:24])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]([Si:30]([CH3:33])([CH3:32])Cl)([CH3:29])([CH3:28])[CH3:27].N1C=CN=C1>>[CH2:1]([O:8][C:9]([C@@H:11]1[N:15]2[C:16](=[O:21])[C@@H:17]([C@H:18]([O:20][Si:30]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:33])[CH3:32])[CH3:19])[C@H:14]2[S:13](=[O:22])(=[O:23])[C:12]1([CH3:24])[CH3:25])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 795Imidazole

HCID 28928tert-Butyldimethylsilyl chloride

HCID 22817303HCID 22817303, compound

Product 1

HCID 70455674HCID 70455674, compound

Procedure

In a manner analogous to that described in Examples (1ba) to (1bc), by reaction of (3S,5R,6R)-2,2-dimethyl-6-[(1R)-1-hydroxyethyl]-penam-3-carboxylic acid benzyl ester 1,1-dioxide (German Offenlegungsschrift No. 3039504) with tert.-butyldimethylchlorosilane and imidazole, (3S,5R,6R)-2,2-dimethyl-6-[(1R)-1-(tert.-butyl-dimethyl-silyloxy)-ethyl]-penam-3-carboxylic acid benzyl ester 1,1-dioxide [IR (methylene chloride): 3.42; 5.56; 5.63μ] is obtained, which is treated with DBU and then with DBU/methyl iodide. The resulting 2-[(3S,4R)-3-((1R)-1-(tert.-butyl-dimethyl-silyloxy)-ethyl)-4-methylsulphonyl-2-oxoazetidin-1-yl]-3-methyl-2-butenoic acid benzyl ester [IR (methylene chloride): 5.63; 5.80; 6.15μ] yields the desired product when ozonolised and subsequently treated with methanol.

Sources & evidence

ORD record: ord-c8b7274bea6543028626f37ec26c39de
Source dataset: uspto-grants-1986_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04616007

Reaction notes

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