Trimethylphosphine → HCID 117600153, compound

HRID 931659Notes

Reaction equation

HRID 931659 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>[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

4

Reactant 2

HCID 68983TrimethylphosphineHCID 117600285HCID 117600285, compound

Product 1

HCID 117600153HCID 117600153, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The crude (S)-7′-azido-4′-fluoro-2′-methoxy-5,6-dihydrospiro[[1,3]oxazine-4,9′-xanthen]-2-amine (1.29 g, 3.63 mmol) was dissolved in THF (27 mL). A THF solution of trimethylphosphine (3.63 mL, 3.63 mmol) was added. After 5 h, the mixture was quenched with 35 mL of 1M aqueous HCl, and the mixture was stiffed overnight. The mixture was then neutralized with saturated NaHCO3 (70 mL) and the aqueous layer mixture was extracted with EtOAc (500 mL). The organic layer was washed with saturated brine (35 mL), dried over MgSO4 and concentrated to afford crude (S)-4′-fluoro-2′-methoxy-5,6-dihydrospiro[[1,3]oxazine-4,9′-xanthene]-2,7′-diamine, which was used without purification in the next step. MS m/z=330 [M+H]+.

Workup

  1. customthe mixture was quenched with 35 mL of 1M aqueous HCl
  2. waitthe mixture was stiffed overnight
  3. extractionthe aqueous layer mixture was extracted with EtOAc (500 mL)
  4. washThe organic layer was washed with saturated brine (35 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d13a3f14c8e34099941a9614490bfe4f
Source dataset
uspto-grants-2016_03
Patent number
US09296759B2

Reaction notes

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