Carbon Disulfide → HCID 54489321, compound

HRID 980969Notes

Reaction equation

[CH3:1][O:2][CH:3]1[CH:6]([S:7][CH3:8])[N:5]([CH2:9][C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[C:4]1=[O:23].C[Si](C)(C)N[Si](C)(C)C.C([Li])CCC.Br[CH2:39][C:40](=[O:42])[CH3:41].[C:43](=[S:45])=[S:44]>>[OH:42][C:40]1([CH3:41])[CH2:39][S:45][C:43](=[C:9]([N:5]2[CH:6]([S:7][CH3:8])[CH:3]([O:2][CH3:1])[C:4]2=[O:23])[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[S:44]1

Participants

Reactant 5

HCID 6348Carbon Disulfide

HCID 11715Bromoacetone

HCID 13838Hexamethyldisilazane

HCID 20220803HCID 20220803, compound

HCID 178418339Butyllithium

Product 1

HCID 54489321HCID 54489321, compound

Procedure

Following the procedure of Preparation 9, but using p-nitrobenzyl 2-(3-methoxy-4-methylthio-2-azetidinon-1-yl)-acetate (151 mg), hexamethyldisilazane (185 μl), butyllithium (540 μl), carbon disulphide (26 μl) and bromoacetone (37 μl), there were obtained 121 mg of the desired product, which was a mixture of two isomers. The isomers were isolated by silica gel column chromatography (eluent: a 6:1 by volume mixture of methylene chloride and ethyl acetate).

Workup

customthe procedure of Preparation 9

Sources & evidence

ORD record: ord-8d9d48633bca4a7190dd43e89a487858
Source dataset: uspto-grants-1987_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04639441

Reaction notes

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