HCID 69388714, compound → HCID 69384236, compound

HRID 916803Notes

Reaction equation

HRID 916803 reaction equation
[CH3:1][C:2]1(C)[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@H:12]3[O:16]C(=O)[N:14]([CH2:18][CH2:19][C:20]4[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][O:29][CH2:30][C:31]5[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=5)=[CH:22][CH:21]=4)[CH2:13]3)=[CH:11][C:5]=2[CH2:4][O:3]1.[O:39]([Si](C)(C)C)[K]>C1COCC1.CO>[C:2]([O:7][C:6]1[CH:8]=[CH:9][C:10]([C@@H:12]([OH:16])[CH2:13][NH:14][CH2:18][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([O:26][CH2:27][CH2:28][O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=3)=[CH:24][CH:25]=2)=[CH:11][C:5]=1[CH2:4][OH:3])(=[O:39])[CH3:1]

Participants

5

Reactant 2

HCID 69388714HCID 69388714, compoundHCID 178504318HCID 178504318, compound

Product 1

HCID 69384236HCID 69384236, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

(5R)-5(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-[2-(4-(2-[(3-fluorobenzyl)oxy]ethoxy}phenyl)ethyl]-1,3-oxazolidin-2-one (125 mg) in THF (1 mL) was treated with KOSiMe3 and the resulting solution was heated at 75° C. for 2 h. The solution was then diluted in MeOH, passed down an SCX-2 cartridge (10 g) and then concentrated in vacuo. The residue was purified by chromatography (SPE, 5 g) eluting with CH2Cl2-MeOH-2M NH3 in MeOH (98:1:1) and then CH2Cl2-MeOH-2M NH3 in MeOH (95:4:1) to give the free base of the title compound. This was converted to the acetate salt using acetic acid to give the title compound (38 mg). LCMS RT=2.56 min. ES+ve 456 (MH)+

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by chromatography (SPE, 5 g)
  3. washeluting with CH2Cl2-MeOH-2M NH3 in MeOH (98:1:1)

Sources & evidence

ORD record
ord-a8df80a899ee4c47b24a226dce89d2ae
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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