Tetrahydrofuran → HCID 69800096, compound

HRID 2179989Notes

Reaction equation

HRID 2179989 reaction equation
[N:1]([CH2:4][CH2:5][C@@H:6]([O:12][C:13]1[CH:20]=[C:19]([CH3:21])[C:18]([F:22])=[CH:17][C:14]=1[C:15]#[N:16])[C:7]1[CH:11]=[CH:10][O:9][N:8]=1)=[N+]=[N-].[O:23]1CCCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:47](=[O:50])([OH:49])[O-].[Na+]>O>[C:10]([OH:23])(=[O:9])/[CH:11]=[CH:7]/[C:47]([OH:49])=[O:50].[NH2:1][CH2:4][CH2:5][C@@H:6]([O:12][C:13]1[CH:20]=[C:19]([CH3:21])[C:18]([F:22])=[CH:17][C:14]=1[C:15]#[N:16])[C:7]1[CH:11]=[CH:10][O:9][N:8]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 86759704HCID 86759704, compound

Product 1

HCID 69800096HCID 69800096, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The solution produced in step (a) was treated with tetrahydrofuran (10 ml), water (1 ml) and triphenylphosphine (0.3 g) and stirred at ambient temperature for 36 h. The mixture was poured into saturated sodium bicarbonate (20 ml) and extracted into ethyl acetate. The extract was evaporated to dryness and the residue loaded onto an ion exchange resin (SCX isolute) and washed with acetonitrile and methanol. The product was eluted off the column with 7M ammonia in methanol to give an oil which was converted into the fumarate salt (0.104 g).

Workup

  1. extractionextracted into ethyl acetate
  2. customThe extract was evaporated to dryness
  3. washwashed with acetonitrile and methanol
  4. washThe product was eluted off the column with 7M ammonia in methanol
  5. customto give an oil which

Sources & evidence

ORD record
ord-33a9eec9f92340689fe603e0cf438d3a
Source dataset
uspto-grants-2005_05
Patent number
US06887871B2

Reaction notes

Loading…