Trimethylphosphine → HCID 117600153, compound

HRID 931651Notes

Reaction equation

HRID 931651 reaction equation
[N:1]([C:4]1[CH:17]=[C:16]2[C:7]([O:8][C:9]3[C:10]([F:26])=[CH:11][C:12]([O:24][CH3:25])=[CH:13][C:14]=3[C@@:15]32[CH2:22][CH2:21][O:20][C:19]([NH2:23])=[N:18]3)=[CH:6][CH:5]=1)=[N+]=[N-].CP(C)C>C1COCC1.O>[F:26][C:10]1[C:9]2[O:8][C:7]3[C:16](=[CH:17][C:4]([NH2:1])=[CH:5][CH:6]=3)[C@@:15]3([CH2:22][CH2:21][O:20][C:19]([NH2:23])=[N:18]3)[C:14]=2[CH:13]=[C:12]([O:24][CH3:25])[CH:11]=1

Participants

5

Reactant 2

HCID 68983TrimethylphosphineHCID 117600285HCID 117600285, compound

Product 1

HCID 117600153HCID 117600153, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-7′-azido-4′-fluoro-2′-methoxy-5,6-dihydrospiro[[1,3]oxazine-4,9′-xanthen]-2-amine (290 mg, 0.816 mmol) in THF (3 ml) and water (1 ml) was added trimethylphosphine (1M in THF) (0.98 ml, 0.98 mmol) and the mixture was stirred at RT for 2 hrs. THF was removed under reduced pressure, water (5 ml) was added and the mixture was extracted with EtOAc. Organic extracts were washed with brine, dried with MgSO4 and concentrated. Recrystallization of the residue from DCM afforded (S)-4′-fluoro-2′-methoxy-5,6-dihydrospiro[[1,3]oxazine-4,9′-xanthene]-2,7′-diamine (102 mg, 0.310 mmol, 38% yield).

Workup

  1. customTHF was removed under reduced pressure, water (5 ml)
  2. additionwas added
  3. extractionthe mixture was extracted with EtOAc
  4. washOrganic extracts were washed with brine
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated
  7. customRecrystallization of the residue from DCM

Sources & evidence

ORD record
ord-3d240b36676b42fca4875cb1c1e0766a
Source dataset
uspto-grants-2016_03
Patent number
US09296759B2

Reaction notes

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