HCID 53395073, compound → HCID 53414540, compound

HRID 1724882Notes

Reaction equation

HRID 1724882 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:46][Si:47]([CH3:50])([CH3:49])[CH3:48])[CH2:9][CH2:10][CH:11](C(NC2C=CC(F)=CC=2)C2C=CC(O[Si](C)(C)C)=CC=2)[C:12]([N:14]2[CH:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)COC2=O)=[O:13])=[CH:4][CH:3]=1>[Cl-].C([P+](CCCC)(CCCC)CCCC)CCC.[Ag-]=O.CCOCC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:14]2[CH:18]([C:19]3[CH:20]=[CH:21][C:22]([O:46][Si:47]([CH3:50])([CH3:49])[CH3:48])=[CH:23][CH:24]=3)[CH:11]([CH2:10][CH2:9][CH:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[O:46][Si:47]([CH3:50])([CH3:49])[CH3:48])[C:12]2=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 53395073HCID 53395073, compound

Product 1

HCID 53414540HCID 53414540, compound

Reagents, catalysts & solvents 3

HCID 75311Tetrabutylphosphonium chlorideCatalystHCID 178418778HCID 178418778, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

3-{5-(4-Fluorophenyl)-2-[(4-fluorophenylamino)-(4-trimethylsilanyloxy-phenyl)methyl]-5-trimethylsilanyloxypentanoyl}-4-phenyloxazolidin-2-one (10 mg) is suspended in MTB ether (1 ml) under argon while cooling in ice. N,O-Bistrimethylsilylacteamide (20.75 μl) is added, followed by tetrabutylphosphonium chloride (4.2 mg) and silver(I) oxide (3.2 mg). The mixture is stirred at room temperature. A reaction to give 1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-trimethylsilanyloxypropyl]-4-(4-trimethylsilanyloxyphenyl)azetidin-2-one is found by means of thin-layer chromatography and LC/MS comparison (M+H,-TMS,-HOTMS: 392).

Workup

  1. temperaturewhile cooling in ice
  2. customA reaction

Sources & evidence

ORD record
ord-c0347651bf6f4d7b9f4e90274e2cb860
Source dataset
uspto-grants-2009_02
Patent number
US07488818B2

Reaction notes

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