Boron trifluoride → HCID 131728665, compound

HRID 1363372Notes

Reaction equation

HRID 1363372 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C@@H:5]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][C:11]([O:16][CH3:17])=[CH:10][C:9]=2[O:18]C)[C@H:4]([OH:20])[CH2:3]1.[C:21](OC(=O)C)(=[O:23])[CH3:22].B(F)(F)F.C([O-])([O-])=O.[Na+].[Na+].[OH-].[Na+]>C(O)(=O)C>[OH:18][C:9]1[C:8]([C@@H:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][C@H:4]2[OH:20])=[C:13]([O:14][CH3:15])[CH:12]=[C:11]([O:16][CH3:17])[C:10]=1[C:21](=[O:23])[CH3:22]

Participants

7

Reactant 5

HCID 6356Boron trifluorideHCID 7918Acetic AnhydrideHCID 10340Sodium Carbonate2×HCID 14798Sodium HydroxideHCID 68880556HCID 68880556, compound

Product 1

HCID 131728665HCID 131728665, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Compound of example 2 (15 g, 53.4 mmol) was reacted with acetic anhydride (27.2 g, 269 mmol) in the presence of BF3-etherate (37.9 g, 267 mmol) at 25° C. The reaction mixture was poured over crushed ice, made basic using saturated Na2CO3 solution. It was extracted using CHCl3 (3×200 mL). The organic extract was washed with water, dried (anhydrous Na2SO4), and concentrated. The solid obtained was treated with 5% aqueous NaOH (85 mL) at 55-60° C. for 1 h. It was diluted with ice water (100 mL), acidified with acetic acid (pH 5), and further basified using aqueous Na2CO3 (pH 9). Filtration afforded the compound which was washed with water and dried to get the title compound.

Workup

  1. additionThe reaction mixture was poured
  2. customover crushed ice
  3. extractionIt was extracted
  4. extractionThe organic extract
  5. washwas washed with water
  6. dry with materialdried (anhydrous Na2SO4)
  7. concentrationconcentrated
  8. customThe solid obtained
  9. filtrationFiltration
  10. customafforded the compound which
  11. washwas washed with water
  12. customdried

Sources & evidence

ORD record
ord-1c8cb71d48cf4263ac0dbcc07e56d7ce
Source dataset
uspto-grants-2011_02
Patent number
US07884127B2

Reaction notes

Loading…