Sodium Hydroxide → HCID 57833618, compound

HRID 730086Notes

Reaction equation

HRID 730086 reaction equation
C[O:2][C:3]([C:5]1[C:18]2[O:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[C:19]3[CH2:25][CH:24]4[N:26]([C:27](=[O:32])C(F)(F)F)[CH:21]([CH2:22][CH2:23]4)[CH2:20]3)[C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].[OH-:33].[Na+]>O1CCOCC1>[C:5]([O:32][C:27]([N:26]1[CH:21]2[CH2:22][CH2:23][CH:24]1[CH2:25][C:19](=[C:10]1[C:9]3[CH:8]=[CH:7][CH:6]=[C:5]([C:3]([OH:2])=[O:4])[C:18]=3[O:17][C:16]3[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:20]2)=[O:33])([CH3:18])([CH3:6])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 15986284HCID 15986284, compound

Product 1

HCID 57833618HCID 57833618, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of compound 7 (2.2 g, 4.96 mmol) in dioxane (25 mL) was added a 3N sodium hydroxide solution (3.5 mL) and the mixture was heated to reflux for 3 h. Additional 3N sodium hydroxide solution (3.5 mL) was added and the mixture was heated to reflux for 16 h. The mixture was allowed to cool to rt and Boc-anhydride (3.24 g, 14.9 mmol) was added. The mixture was stirred for 24 h at rt, the solvent was evaporated, and the residue was partitioned between water and ethyl acetate. The organic phase was separated, dried over sodium sulfate, filtered, and evaporated. The residue was used without further purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 h
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 16 h
  5. customthe solvent was evaporated
  6. customthe residue was partitioned between water and ethyl acetate
  7. customThe organic phase was separated
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was used without further purification

Sources & evidence

ORD record
ord-b2b78cc09fbe49aab6cfd43206643891
Source dataset
uspto-grants-2009_09
Patent number
US07582650B2

Reaction notes

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