Water → HCID 69804252, compound

HRID 2179975Notes

Reaction equation

HRID 2179975 reaction equation
[N:1]([CH2:4][CH2:5][C@@H:6]([O:12][C:13]1[CH:20]=[C:19]([Cl:21])[C:18]([F:22])=[CH:17][C:14]=1[C:15]#[N:16])[C:7]1[CH:11]=[CH:10][S:9][CH:8]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.[C:43]([OH:48])(=[O:47])[C:44]([OH:46])=[O:45]>O1CCCC1>[C:43]([OH:48])(=[O:47])[C:44]([OH:46])=[O:45].[NH2:1][CH2:4][CH2:5][C@@H:6]([O:12][C:13]1[CH:20]=[C:19]([Cl:21])[C:18]([F:22])=[CH:17][C:14]=1[C:15]#[N:16])[C:7]1[CH:11]=[CH:10][S:9][CH:8]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 971Oxalic AcidHCID 11776TriphenylphosphineHCID 91580323HCID 91580323, compound

Product 1

HCID 69804252HCID 69804252, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from step (a) (529 mg, 1.57 mmol) was dissolved in anhydrous tetrahydrofuran (80 ml), triphenylphosphine (1.235 g, 4.71 mmol) added and the reaction mixture stirred for 1 h at room temperature. Water (5 ml) was added and the reaction stirred for 64 h. Water (100 ml) was added and the reaction extracted with ethyl acetate (4×70 ml). The combined organic extracts were washed with water (3×25 ml), dried (sodium sulphate) and evaporated in vacuo. The residue was chromatographed on flash silica, eluting with 5% 7N ammonia in methanol in dichloromethane, and the product dissolved in methanol and treated with one equivalent of oxalic acid. The mixture was stirred for 10 minutes then the solvent removed in vacuo and the solid residue triturated with ethyl acetate. The white solid was filtered off and dried to give the title compound (380 mg, 60%).

Workup

  1. stirringthe reaction stirred for 64 h
  2. extractionthe reaction extracted with ethyl acetate (4×70 ml)
  3. washThe combined organic extracts were washed with water (3×25 ml)
  4. dry with materialdried (sodium sulphate)
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on flash silica
  7. washeluting with 5% 7N ammonia in methanol in dichloromethane
  8. dissolutionthe product dissolved in methanol
  9. stirringThe mixture was stirred for 10 minutes
  10. customthe solvent removed in vacuo
  11. customthe solid residue triturated with ethyl acetate
  12. filtrationThe white solid was filtered off
  13. customdried

Sources & evidence

ORD record
ord-4d5e2ae9eb1c4d0da3df9d711d00238d
Source dataset
uspto-grants-2005_05
Patent number
US06887871B2

Reaction notes

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