Triethylamine → HCID 66890038, compound

HRID 547992Notes

Reaction equation

HRID 547992 reaction equation
[CH2:1]([O:8][C@H:9]([C@@H:29]([C@H:38]([CH2:51][O:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[O:39]C(=O)C1C=CC([N+]([O-])=O)=CC=1)[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:10][O:11][Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].C(N(CC)CC)C.F.F.F.C(N(CC)CC)C>CO>[CH2:1]([O:8][C@H:9]([C@@H:29]([C@H:38]([CH2:51][O:52][CH2:53][C:54]1[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=1)[OH:39])[O:30][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 175505N,N-Diethylethanamine trihydrofluorideHCID 10942334Sodium MethoxideHCID 91092123HCID 91092123, compound

Product 1

HCID 66890038HCID 66890038, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 6 (110 g, 138.54 mmole) was dissolved in methanol (500 mL) and sodium methoxide (11 g, 204.0 mmole, 1.5 eq.) was added and the solution was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and the residue was partitioned between ether and water. The separated organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was dried in vacuo for 3 hrs and dissolved in dry THF under nitrogen. Triethylamine (TEA) (100 mL, 0.752 mole, 5 eq.) was added followed by triethylamine trihydrofluoride (TREAT.HF) (220 mL, 1.38 mole, 10 eq.) and the mixture was stirred overnight at room temperature. The solvent was removed under reduced pressure and the residue partitioned between ether and water. The ether layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue purified by flash chromatography (40% ethyl acetate in hexane) to give 51 g of compound 7 in 90% yield (reported literature yield 81%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between ether and water
  3. washThe separated organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was dried in vacuo for 3 hrs
  7. dissolutiondissolved in dry THF under nitrogen
  8. stirringthe mixture was stirred overnight at room temperature
  9. customThe solvent was removed under reduced pressure
  10. customthe residue partitioned between ether and water
  11. washThe ether layer was washed with brine
  12. dry with materialdried over anhydrous sodium sulfate
  13. customThe solvent was removed under reduced pressure
  14. customthe residue purified by flash chromatography (40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-536b685c05cc4558b27816025207d108
Source dataset
uspto-grants-2011_05
Patent number
US07939677B2

Reaction notes

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