tert-Butyl methyl ether → 3-[3-(tert-Butyl-dimethyl-silanyloxy)-3-phenyl-propyl]-4-(3-methoxy-phenyl)-1-(4-nitro-phenyl)-azetidin-2-on

HRID 2115189Notes

Reaction equation

HRID 2115189 reaction equation
[C:1]([Si:5]([CH3:51])([CH3:50])[O:6][CH:7]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[CH2:8][CH2:9][CH:10]([CH:25]([C:36]1[CH:41]=[CH:40][C:39](OC)=[CH:38][CH:37]=1)[NH:26][C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1)[C:11](N1C(C2C=CC=CC=2)COC1=O)=[O:12])([CH3:4])([CH3:3])[CH3:2].C[Si](C([Si](C)(C)C)[C:57](N)=[O:58])(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OC)(C)(C)C>C(O)(=O)C>[C:1]([Si:5]([CH3:51])([CH3:50])[O:6][CH:7]([C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)[CH2:8][CH2:9][CH:10]1[CH:25]([C:36]2[CH:37]=[CH:38][CH:39]=[C:40]([O:58][CH3:57])[CH:41]=2)[N:26]([C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=2)[C:11]1=[O:12])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 2724141Tetrabutylammonium FluorideHCID 11708267BistrimethylsilylacetamidHCID 686400833-{5-(tert-Butyl-dimethyl-silanyloxy)-2-[(4-methoxy-phenyl)-(4-nitro-phenylamino)-methyl]-5-phenyl-pentanoyl}-4-phenyl-oxazolidin-2-on

Product 1

HCID 686397133-[3-(tert-Butyl-dimethyl-silanyloxy)-3-phenyl-propyl]-4-(3-methoxy-phenyl)-1-(4-nitro-phenyl)-azetidin-2-onYield 70%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture comprising 6.1 g (8.6 mmol) of product 3, 7.3 ml of bistrimethylsilylacetamid, 0.5 g of Tetrabutylammoniumfluorid and 100 ml of tert -butylmethylether is stirred under a argon atmosphere for 10 h at room temperature. After finishing of the reaction 5 ml of acetic acid are added slowly by cooling with ice and evaporated. The residue is separated by chromatography on silica gel (ethylacetate/heptane=1/2). 3.3 g (70%) of product 4 is obtained in form of a light yellow compound in solid form: C31H38N2O5Si (546.74) MS (ESI+) 547.3 (M+H+).

Workup

  1. additionare added slowly
  2. temperatureby cooling with ice
  3. customevaporated
  4. customThe residue is separated by chromatography on silica gel (ethylacetate/heptane=1/2)

Sources & evidence

ORD record
ord-3243c7ba09e54be38107f97cf59edb54
Source dataset
uspto-grants-2008_10
Patent number
US07435727B2

Reaction notes

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