tert-Butyldimethylsilyl chloride → HCID 54479352, compound

HRID 863652Notes

Reaction equation

HRID 863652 reaction equation
[C:1]([O:4][C@@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[NH:10][C:11](=[O:19])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:3])[CH3:2].[C:20]([Si:24]([CH3:27])([CH3:26])Cl)([CH3:23])([CH3:22])[CH3:21]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:1]([O:4][C@@H:5]1[N:8]([Si:24]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:27])[CH3:26])[C:7](=[O:9])[C@H:6]1[NH:10][C:11](=[O:19])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 10923331HCID 10923331, compound

Product 1

HCID 54479352HCID 54479352, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Such a preferred procedure comprises treating the (3S,4S)-4-acetoxy-3-phenylacetamido-azetidin-2-one (II) with tert-butyldimethyl chlorosilane in the presence of 4-dimethylaminopyridine and, optionally, of pyridine in an organic solvent, isolating the (3S,4S)-4-acetoxy-3-phenylacetamido-1-tert-butyldimethylsilyl-azetidin-2-one (III) thus obtained and treating with an inorganic sulfide to obtain (3S,4S)-4-acetoxy-3-phenylethanethioylamino-1-tert-butyldime thylsilyl-azetidin-2-one (IV) and treating this compound with a base in an organic solvent at a temperature of 70°÷130° C.

Sources & evidence

ORD record
ord-fe5986b5c3724094a70696e5dcebc340
Source dataset
uspto-grants-1998_02
Patent number
US05721360

Reaction notes

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