Trimethylphosphine → HCID 59635958, compound

HRID 563904Notes

Reaction equation

HRID 563904 reaction equation
[N:1]([C@H:4]1[C@:14]2([CH3:16])[O:15][C@@:6]3([C@H:17]4[C@H:10]([N:11]([C:19]5[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([C:27]([F:30])([F:29])[F:28])[CH:20]=5)[C:12](=[O:18])[C@@H:13]24)[O:9][CH2:8][CH2:7]3)[CH2:5]1)=[N+]=[N-].P(C)(C)C>C1COCC1>[NH2:1][C@H:4]1[C@:14]2([CH3:16])[O:15][C@@:6]3([C@H:17]4[C@H:10]([N:11]([C:19]5[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([C:27]([F:28])([F:29])[F:30])[CH:20]=5)[C:12](=[O:18])[C@@H:13]24)[O:9][CH2:8][CH2:7]3)[CH2:5]1

Participants

4

Reactant 2

HCID 68983TrimethylphosphineHCID 59635864HCID 59635864, compound

Product 1

HCID 59635958HCID 59635958, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To Example 12 (10.3 g, 0.0246 mol) in THF (50 mL) cooled in a water bath was added PMe3 (49 mL, 1M in THF). The mixture was stirred for 10 min then the solvent was removed in vacuo. The residue was dissolved in MeOH (30 mL) and 50% NaOH (0.7 mL, aq) was added. The mixture was stirred for 30 min and then concentrated in vacuo. To the residue was added water and brine and then extracted twice with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The resulting solid was triturated with EtOAc/hexane (100 mL, 1:1) and filtered with EtOAc/hexane rinse, then dried to afford 8.8 g of Example 13.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in MeOH (30 mL)
  3. addition50% NaOH (0.7 mL, aq) was added
  4. stirringThe mixture was stirred for 30 min
  5. concentrationconcentrated in vacuo
  6. additionTo the residue was added water and brine
  7. extractionextracted twice with EtOAc
  8. dry with materialThe organic layer was dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe resulting solid was triturated with EtOAc/hexane (100 mL, 1:1)
  12. filtrationfiltered with EtOAc/hexane
  13. washrinse
  14. customdried

Sources & evidence

ORD record
ord-43bb986dda1a4fb2a3b6f6b824a388e5
Source dataset
uspto-grants-2011_11
Patent number
US08067582B2

Reaction notes

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