Cesium carbonate → HCID 67358825, compound

HRID 577959Notes

Reaction equation

HRID 577959 reaction equation
[Si]([O:18][CH2:19][C:20]1[C:21]([N:39]2[CH2:44][C@H:43]([CH3:45])[O:42][C@H:41]([CH3:46])[CH2:40]2)=[C:22]([F:38])[C:23](F)=[C:24]([C:26](=[N:35][OH:36])[C:27]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[O:28])[CH:25]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[CH3:46][C@@H:41]1[CH2:40][N:39]([C:21]2[C:20]([CH2:19][OH:18])=[CH:25][C:24]3[C:26]([C:27]([N:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)=[O:28])=[N:35][O:36][C:23]=3[C:22]=2[F:38])[CH2:44][C@H:43]([CH3:45])[O:42]1

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 86717866HCID 86717866, compound

Product 1

HCID 67358825HCID 67358825, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-(5-((tert-Butyldiphenylsilyloxy)methyl)-4-((2R,6S)-2,6-dimethylmorpholino)-2,3-difluorophenyl)-2-(hydroxyimino)-1-morpholinoethanone, (Intermediate 168, 133 mg, 0.20 mmol) was dissolved in DMF and stirred at 60° C. with cesium carbonate (332 mg, 1.02 mmol) for 6 hours. The reaction stirred at room temperature over 2 days. The reaction was diluted with water and extracted three times with ethyl acetate. The organic layers were combined and washed 5× with brine, dried over MgSO4 and concentrated to give an oil. The oil was purified by silica gel column chromatography using a gradient of hexanes to ethyl acetate to give the title compound (34 mg, 0.086 mmol).

Workup

  1. extractionextracted three times with ethyl acetate
  2. washwashed 5× with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto give an oil
  6. customThe oil was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f9503c1cf07648d0876c37fb8dd4cdd8
Source dataset
uspto-grants-2015_05
Patent number
US09040528B2

Reaction notes

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