Acetic Acid → 3-[3-(tert-Butyldimethylsilanyloxy)-3-(4-fluorophenyl)propyl]-1-(4-fluorophenyl)-4-(4-hydroxyphenyl)azetidin-2-one

HRID 1612541Notes

Reaction equation

HRID 1612541 reaction equation
[Si:1]([O:8][CH:9]([C:43]1[CH:48]=[CH:47][C:46]([F:49])=[CH:45][CH:44]=1)[CH2:10][CH2:11][CH:12]([CH:27]([NH:35][C:36]1[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=1)[C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1)[C:13](N1C(C2C=CC=CC=2)COC1=O)=[O:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C[Si](C([Si](C)(C)C)C(N)=O)(C)C.O.O.O.[F-].C([NH+](CCCC)CCCC)CCC.C(O)(=O)C>COC(C)(C)C>[Si:1]([O:8][CH:9]([C:43]1[CH:48]=[CH:47][C:46]([F:49])=[CH:45][CH:44]=1)[CH2:10][CH2:11][CH:12]1[CH:27]([C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=2)[N:35]([C:36]2[CH:37]=[CH:38][C:39]([F:42])=[CH:40][CH:41]=2)[C:13]1=[O:14])([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 11708267BistrimethylsilylacetamidHCID 222520473-(5-(Tert-butyldimethylsilanyloxy)-5-(4-fluorophenyl)-2-[(4-fluorophenyl-amino)-(4-hydroxyphenyl)methyl]pentanoyl)-4-phenyloxazolidin-2-oneHCID 22252057Tributylammonium fluoride trihydrate

Product 1

HCID 222520743-[3-(tert-Butyldimethylsilanyloxy)-3-(4-fluorophenyl)propyl]-1-(4-fluorophenyl)-4-(4-hydroxyphenyl)azetidin-2-one

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

2.63 g of 3-{5-(tert-butyldimethylsilanyloxy)-5-(4-fluorophenyl)-2-[(4-fluorophenyl-amino)-(4-hydroxyphenyl)methyl]pentanoyl}-4-phenyloxazolidin-2-one are suspended in 60 ml of tert-butyl methyl ether. 3.22 ml of bis(trimethylsilyl)acetamide and 122 mg of tributylammonium fluoride trihydrate are then added. The reaction mixture is stirred at room temperature for 3 h, and 0.6 ml of glacial acetic acid are then added. The reaction mixture is concentrated using a rotary evaporator and the residue is purified by column chromatography (SiO2; ethyl acetate/heptane 1:4). The product is obtained as clear crystals. C30H35F2NO3Si (523) MS (ESI): M+−131

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customa rotary evaporator
  3. customthe residue is purified by column chromatography (SiO2; ethyl acetate/heptane 1:4)
  4. customThe product is obtained as clear crystals

Sources & evidence

ORD record
ord-bb323d7095964be0b876fb05546c77f0
Source dataset
uspto-grants-2006_01
Patent number
US06992067B2

Reaction notes

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