Imidazole → HCID 68881841, compound

HRID 536700Notes

Reaction equation

HRID 536700 reaction equation
[CH:1]([C:3]1[C@H:12]([CH2:13][O:14][Si:15]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])[C@@H:11]([OH:25])[C:10]2[C:5](=[CH:6][C:7]3[O:28][CH2:27][O:26][C:8]=3[CH:9]=2)[CH:4]=1)=[O:2].N1[CH:33]=[CH:32]N=C1.[O-]Cl=O.[Na+].[OH2:38]>CN(C=O)C>[CH2:27]1[O:28][C:7]2[CH:6]=[C:5]3[C:10]([C@H:11]([O:25][Si:15]([CH2:32][CH3:33])([CH2:19][CH3:20])[CH2:16][CH3:17])[C@@H:12]([CH2:13][O:14][Si:15]([CH:16]([CH3:18])[CH3:17])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:20])[CH3:21])[C:3]([C:1]([OH:38])=[O:2])=[CH:4]3)=[CH:9][C:8]=2[O:26]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962Water2×HCID 10993149HCID 10993149, compoundHCID 23668197Sodium Chlorite

Product 1

HCID 68881841HCID 68881841, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of aldehyde 11 (900 mg, 2.25 mmol) in DMF (20 mL) was added TESCI (715 JtL, 3.38 mmol) and imidazole (460 mg, 6.75 mmol) at 0° C. and the reaction mixture was allowed to warm to r.t. overnight. Water was added and the product was extracted with Et20, the organic layer dried over MgSO4 and evaporated. The residue was then dissolved in t-BuOH (40 mL) and 2-methyl-2-butene (12 mL). A solution of NaClO2 (1.81 g, 20 mmol) and NaH2PO4 (1.93 g) in water (20 mL) was added and the mixture was stirred overnight. The product was extracted with Et2O, dried over MgSO4, concentrated and purified by silica gel column chromatography (10-30% EtOAc in hexanes) to give the acid 12 as a white powder (1.02 g, 85% over 2 steps). 1H NMR (400 MHz, CDCl3) 00.65 (q, J=8.0 Hz, 6H), 0.94 (t, J=8.0 Hz, 9H), 1.06 (m, 21H), 3.05, (apt t, J=10 Hz, 1H), 3.34 (ddd, J=10.0, 4.5, 1.6 Hz, 1H), 3.77 (dd, J=10.0, 4.5 Hz, 1H), 5.03 (s, 1H), 6.03 (s, 2H), 6.81 (d, J=4.8 Hz, 2H), 7.67 (s, 1H).

Workup

  1. extractionthe product was extracted with Et20
  2. dry with materialthe organic layer dried over MgSO4
  3. customevaporated
  4. dissolutionThe residue was then dissolved in t-BuOH (40 mL)
  5. extractionThe product was extracted with Et2O
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. custompurified by silica gel column chromatography (10-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-5899623957494f478645c429442cf23e
Source dataset
uspto-grants-2014_10
Patent number
US08859614B2

Reaction notes

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