Peracetic Acid → HCID 71281752, compound

HRID 1481784Notes

Reaction equation

HRID 1481784 reaction equation
[CH2:1]([O:8][C:9]1[N:24]=[CH:23][C:22](I)=[C:21]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Mg]Cl)(C)C.[Li+].[Cl-].B(OC(C)C)(OC(C)C)[O:42]C(C)C.C(OO)(=O)C>C1COCC1.O>[CH2:1]([O:8][C:9]1[N:24]=[CH:23][C:22]([OH:42])=[C:21]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6585Peracetic AcidHCID 21531Triisopropyl borateHCID 71281816HCID 71281816, compoundHCID 178461733HCID 178461733, compound

Product 1

HCID 71281752HCID 71281752, compoundYield 36.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-45 °C

Procedure

Into a solution of benzyl 2,4-bis(benzyloxy)-5-iodonicotinate (1.0 g, 1.8 mmol) in THF (8.0 mL) at −45° C. was added a solution of i-PrMgCl—LiCl (1.3 M×2.8 mL, 3.6 mmol) dropwise. The mixture was stirred at −45° C. for 30 min, into which triisopropyl borate (0.87 mL, 3.78 mmol) was added dropwise. After stirring at −45° C. for 15 min, the temperature was allowed to rise to room temperature slowly. The mixture was stirred at room temperature for 1.5 h then cooled to −20° C., into which peracetic acid (32%, 0.79 mL, 3.78 mmol) was added. The mixture was stirred at room temperature for another 30 min before it was treated with water (50 mL). The mixture was extracted with ethyl acetate. The organic layers were combined and washed with brine, dried over sodium sulfate, evaporated and purified by silica chromatography (0-30% ethyl acetate in hexanes) to give benzyl 2,4-bis(benzyloxy)-5-hydroxynicotinate (0.29 g, 36%).

Workup

  1. additionwas added dropwise
  2. customto rise to room temperature
  3. stirringThe mixture was stirred at room temperature for 1.5 h
  4. additionwas added
  5. stirringThe mixture was stirred at room temperature for another 30 min before it
  6. extractionThe mixture was extracted with ethyl acetate
  7. washwashed with brine
  8. dry with materialdried over sodium sulfate
  9. customevaporated
  10. custompurified by silica chromatography (0-30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-32f3dc230177495eada0c348f9c4138f
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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