tert-Butanol → HCID 18182398, compound

HRID 1359317Notes

Reaction equation

HRID 1359317 reaction equation
[CH2:1]([C:8]1[C:9]([O:17][CH3:18])=[N:10][CH:11]=[C:12](C(O)=O)[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:26])C=CC=CC=1.C([N:38]([CH2:41]C)CC)C.[C:43]([OH:47])([CH3:46])([CH3:45])[CH3:44]>>[CH2:1]([C:8]1[C:9]([O:17][CH3:18])=[N:10][CH:11]=[C:12]([NH:38][C:41]([O:47][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:26])[CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 18182316HCID 18182316, compound

Product 1

HCID 18182398HCID 18182398, compound

Procedure

7.34 g of 3-benzyl-2-methoxypyridine-5-carboxylic acid (Example 35-a), 6.5 ml of diphenylphosphorylazide and 4.2 ml of triethylamine were mixed in 100 ml of tert-butanol, followed by heating under reflux overnight. After evaporating the reaction solution, it was partitioned by adding water and ethyl acetate thereto, washed with brine, dried over anhydrous magnesium sulfate and then evaporated. The residue was subjected to silica gel column chromatography, to synthesize 9.37 g of the target compound.

Workup

  1. temperatureby heating
  2. temperatureunder reflux overnight
  3. customAfter evaporating the reaction solution, it
  4. customwas partitioned
  5. additionby adding water and ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated
  9. customto synthesize 9.37 g of the target compound

Sources & evidence

ORD record
ord-91ef1f75963749778b61012d5e77d7db
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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