Di-tert-butyl diethylphosphoramidite → HCID 67279775, compound

HRID 1694666Notes

Reaction equation

HRID 1694666 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:33]([F:36])([F:35])[F:34])[CH:5]=[C:6]([C:8]2[O:9][CH:10]=[C:11]([CH2:13][O:14][C:15]3[CH:24]=[C:23]4[C:18]([C:19](=[O:32])[C:20]([C:25]5[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=5)=[CH:21][O:22]4)=[CH:17][CH:16]=3)[N:12]=2)[CH:7]=1.N1C=NN=N1.C(N(CC)[P:45]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])[O:46][C:47]([CH3:50])([CH3:49])[CH3:48])C>O1CCCC1.C(Cl)Cl>[C:52]([O:51][P:45]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])[O:31][C:28]1[CH:27]=[CH:26][C:25]([C:20]2[C:19](=[O:32])[C:18]3[C:23](=[CH:24][C:15]([O:14][CH2:13][C:11]4[N:12]=[C:8]([C:6]5[CH:7]=[C:2]([F:1])[CH:3]=[C:4]([C:33]([F:34])([F:36])[F:35])[CH:5]=5)[O:9][CH:10]=4)=[CH:16][CH:17]=3)[O:22][CH:21]=2)=[CH:30][CH:29]=1)([CH3:55])([CH3:54])[CH3:53]

Participants

6

Reactant 3

HCID 4251849Di-tert-butyl diethylphosphoramiditeHCID 42605467HCID 42605467, compoundHCID 178418441HCID 178418441, compound

Product 1

HCID 67279775HCID 67279775, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-({2-[5-fluoro-3-(trifluoromethyl)phenyl](1,3-oxazol-4-yl)}methoxy)-3-(4-hydroxyphenyl)chromen-4-one (1 g, 2.01 mmol) in tetrahydrofuran (50 mL) was added 1-H-tetrazole (3% wt in acetonitrile, 65 ml, 22.1 mmol), followed by di-tert-butyl N,N-diethylphosphoramidite (2.57 ml, 4.6 mmol). After stirring at room temperature for 2 hours, the reaction mixture was diluted with methylene chloride and washed with saturated sodium bicarbonate. The organic layer was separated, and the aqueous layer extracted twice more with methylene chloride. The combined extracts were dried over sodium sulfate, and solvent removed under reduced pressure. The residue was purified by biotage column chromatography, eluting with ethyl acetate/hexane mixture (1:4) to afford 3-{4-[bis(tert-butoxy)phosphinooxy]phenyl}-7-({2-[5-fluoro-3-(trifluoromethyl)phenyl](1,3-oxazol-4-yl)}methoxy)chromen-4-one.

Workup

  1. washwashed with saturated sodium bicarbonate
  2. customThe organic layer was separated
  3. extractionthe aqueous layer extracted twice more with methylene chloride
  4. dry with materialThe combined extracts were dried over sodium sulfate, and solvent
  5. customremoved under reduced pressure
  6. customThe residue was purified by biotage column chromatography
  7. washeluting with ethyl acetate/hexane mixture (1:4)

Sources & evidence

ORD record
ord-b99ddaf3e7904dffa2f9213c72adcd25
Source dataset
uspto-grants-2012_04
Patent number
US08158810B2

Reaction notes

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