HCID 69386463, compound → HCID 69385147, compound

HRID 916807Notes

Reaction equation

HRID 916807 reaction equation
[CH3:1][C:2]1([CH3:39])[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:38]=[CH:37][C:23]([O:24][CH2:25][CH2:26][O:27][CH2:28][C:29]5[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=5)[C:32]#[N:33])=[CH:22][CH:21]=4)[CH2:13]3)=[CH:11][C:5]=2[CH2:4][O:3]1.[O:40]([Si](C)(C)C)[K]>C1COCC1>[NH3:14].[CH3:2][OH:3].[CH3:39][C:2]1([CH3:1])[O:3][C:4]2[CH:5]=[CH:11][C:10]([C@@H:12]([OH:16])[CH2:13][NH:14][CH2:18][CH2:19][C:20]3[CH:38]=[CH:37][C:23]([O:24][CH2:25][CH2:26][O:27][CH2:28][C:29]4[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=4)[C:32]([NH2:33])=[O:40])=[CH:22][CH:21]=3)=[CH:9][C:8]=2[CH2:6][O:7]1

Participants

5

Reactant 2

HCID 69386463HCID 69386463, compoundHCID 178504318HCID 178504318, compound

Product 2

HCID 21705897Ammonia methanolHCID 69385147HCID 69385147, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

3-{[2-(4-{2-[(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]ethyl}phenoxy)ethoxy]methyl}benzonitrile (125 mg) in THF (3 mL) was treated with KOSiMe3 (152 mg) and the resulting solution was heated at 75° C. for 4 h. The reaction mixture was then quenched with MeOH and concentrated in vacuo. The residue was taken up in EtOAc, washed with phosphate buffer (pH=6.5) and water, dried (MgSO4) and concentrated in vacuo. The residue was purified by chromatography (SPE, 5 g) eluting with CH2Cl2-MeOH-2M NH3 in MeOH (196:3:1) and then CH2Cl2: MeOH: 2M NH3/MeOH (96:3:1) to give the title compound (42 mg). LCMS RT=2.40 min.

Workup

  1. customThe reaction mixture was then quenched with MeOH
  2. concentrationconcentrated in vacuo
  3. washwashed with phosphate buffer (pH=6.5) and water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography (SPE, 5 g)
  7. washeluting with CH2Cl2-MeOH-2M NH3 in MeOH (196:3:1)

Sources & evidence

ORD record
ord-48b7fbaa51fe46b480f156c54f811227
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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