Potassium trimethylsilanolate → HCID 69386530, compound

HRID 916836Notes

Reaction equation

HRID 916836 reaction equation
CC1(C)OC2C=CC([C@H]3OC(=O)[N:14](CCC4C=CC(OCCOCC5C=CC=C(S(C(C)C)=O)C=5)=CC=4)C3)=CC=2C[O:3]1.[CH3:43][C:44]1(C)[O:49][C:48]2[CH:50]=[CH:51][C:52]([C@@H:54]([OH:81])[CH2:55][NH:56][CH2:57][CH2:58][C:59]3[CH:64]=[CH:63][C:62]([O:65][CH2:66][CH2:67][O:68][CH2:69][C:70]4[CH:75]=[CH:74][CH:73]=[C:72]([S:76]([CH:78]([CH3:80])[CH3:79])=[O:77])[CH:71]=4)=[CH:61][CH:60]=3)=[CH:53][C:47]=2[CH2:46][O:45]1.C[Si](C)(C)[O-].[K+]>C1COCC1.ClCCl>[NH3:14].[C:44]([O:49][C:48]1[CH:50]=[CH:51][C:52]([C@@H:54]([OH:81])[CH2:55][NH:56][CH2:57][CH2:58][C:59]2[CH:64]=[CH:63][C:62]([O:65][CH2:66][CH2:67][O:68][CH2:69][C:70]3[CH:75]=[CH:74][CH:73]=[C:72]([S:76]([CH:78]([CH3:80])[CH3:79])=[O:77])[CH:71]=3)=[CH:61][CH:60]=2)=[CH:53][C:47]=1[CH2:46][OH:3])(=[O:45])[CH3:43]

Participants

6

Reactant 2

HCID 23668039Potassium trimethylsilanolateHCID 86601665HCID 86601665, compound

Product 2

HCID 222AmmoniaHCID 69386530HCID 69386530, compoundYield 90.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

(1R)-1-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-({2-[4-(2-{[3-(isopropylsulfinyl)benzyl]oxy}ethoxy)phenyl]ethyl}amino)ethanol (5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-{2-[4-(2-{[3-(isopropylsulfinyl)benzyl]oxy}ethoxy)phenyl]ethyl}-1,3-oxazolidin-2-one (0.07 g) was stirred with potassium trimethylsilanolate (0.14 g) in THF (5 ml) under reflux for 2.5 h. After cooling the mixture was diluted with dichloromethane and poured onto a 10 g Bond Elut silica cartridge which was eluted successively with dichloromethane, then dichloromethane:ethanol:0.880 ammonia solution (100:8:1 and then 50:8:1) to give the title compound (0.031 g). LCMS RT=2.61 min. vi) 4-[(1R)-1-Hydroxy-2-({2-[4-(2-{[3-(isopropylsulfinyl)benzyl]oxy}ethoxy)phenyl]ethyl}amino)ethyl]-2-(hydroxymethyl)phenol acetate

Workup

  1. temperatureunder reflux for 2.5 h
  2. temperatureAfter cooling the mixture
  3. additionpoured onto a 10 g Bond Elut silica cartridge which
  4. washwas eluted successively with dichloromethane

Sources & evidence

ORD record
ord-5a4db7c344b34e4fb76b571aae900c1a
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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