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

HRID 506842Notes

Reaction equation

HRID 506842 reaction equation
[C:1]([Si:5]([CH3:39])([CH3:38])[O:6][CH:7]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:8][CH2:9][CH:10]1[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)[N:12]([C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-])=O)=[CH:24][CH:23]=2)[C:11]1=[O:31])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(OC(=O)C)C.[Pd]>[NH2:28][C:25]1[CH:26]=[CH:27][C:22]([N:12]2[CH:13]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=3)[CH:10]([CH2:9][CH2:8][CH:7]([O:6][Si:5]([C:1]([CH3:3])([CH3:2])[CH3:4])([CH3:38])[CH3:39])[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:11]2=[O:31])=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 686397133-[3-(tert-Butyl-dimethyl-silanyloxy)-3-phenyl-propyl]-4-(3-methoxy-phenyl)-1-(4-nitro-phenyl)-azetidin-2-onHCID 178418361HCID 178418361, compound

Product 1

HCID 686400691-(4-Amino-phenyl)-3-[3-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-propyl]-4-(3-methoxy-phenyl)-azetidin-2-onYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A reaction is performed with 3.0 g (5.5 mmol) of product 4 in 50 ml ethylacetate and 1.0 g of palladium charcoal 10% for 2 h at 5 bar of a hydrogen atmosphere using an autoclave. The reaction solution is filtrated, evaporated and separated by chromatography on silica gel (methylenehloride/methanol=10/1). 2.4 g (86%) of product 5 is obtained in form of a colourless compound in solid form: C31H40N2O3Si (516.76) MS (ESI+) 517.4 (M+H+).

Workup

  1. filtrationThe reaction solution is filtrated
  2. customevaporated
  3. customseparated by chromatography on silica gel (methylenehloride/methanol=10/1)

Sources & evidence

ORD record
ord-d3ec46ba7c144d1397e9c8f9da063ee7
Source dataset
uspto-grants-2010_08
Patent number
US07786103B2

Reaction notes

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