Pyridine → HCID 22857741, compound

HRID 2259514Notes

Reaction equation

HRID 2259514 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C@H:10]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][O:27]C2CCCCO2)[CH:21]=1)[O:11][CH2:12][C:13]1([CH2:16][C:17]([OH:19])=[O:18])[CH2:15][CH2:14]1.[CH2:34]1COCC1.N1C=CC=CC=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CCOCC>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C@H:10]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][OH:27])[CH:21]=1)[O:11][CH2:12][C:13]1([CH2:16][C:17]([O:19][CH3:34])=[O:18])[CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 22857727HCID 22857727, compound

Product 1

HCID 22857741HCID 22857741, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The acid of Step 7 (1.816 g, 3.51 mmol) was esterified with CH2N2 at 0° C. in ether:THF. The excess CH2N2 was quenched with AcOH and the product was concentrated and stripped with toluene twice. This ester was dissolved in 20 mL MeOH and then pyridine (7 μL) and pyridinium p-toluenesulfonate (220 mg, 0.88 mmol) were added. After 6 days of stirring, the solvent was evaporated. 25% aq. NH4OAc was then added and the product was extracted in EtOAc, dried over Na2SO4, and purified by flash chromatography on silica with EtOAc:hexane 30:70; yield: 1.53 g, (97%).

Workup

  1. customThe excess CH2N2 was quenched with AcOH
  2. concentrationthe product was concentrated
  3. dissolutionThis ester was dissolved in 20 mL MeOH
  4. customthe solvent was evaporated
  5. addition25% aq. NH4OAc was then added
  6. extractionthe product was extracted in EtOAc
  7. dry with materialdried over Na2SO4
  8. custompurified by flash chromatography on silica with EtOAc:hexane 30:70

Sources & evidence

ORD record
ord-daf242563b814d5f926961e48bb96fce
Source dataset
uspto-grants-1995_12
Patent number
US05472964

Reaction notes

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