Triacetoxyperiodinane → HCID 90204216, compound

HRID 1480199Notes

Reaction equation

HRID 1480199 reaction equation
[CH:1]1([C:4]2[C:5]([O:23][CH2:24][C:25]([F:28])([F:27])[F:26])=[CH:6][C:7]([C:10]([NH:12][C:13]([C:17]3[N:21]=[C:20]([CH3:22])[O:19][N:18]=3)([CH3:16])[CH2:14][OH:15])=[O:11])=[N:8][CH:9]=2)[CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[CH:1]1([C:4]2[C:5]([O:23][CH2:24][C:25]([F:26])([F:27])[F:28])=[CH:6][C:7]([C:10]([NH:12][C:13]([CH3:16])([C:17]3[N:21]=[C:20]([CH3:22])[O:19][N:18]=3)[CH:14]=[O:15])=[O:11])=[N:8][CH:9]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 76284755HCID 76284755, compound

Product 1

HCID 90204216HCID 90204216, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-cyclopropyl-N-[1-hydroxy-2-(5-methyl-1,2,4-oxadiazol-3-yl)propan-2-yl]-4-(2,2,2-trifluoroethoxy)pyridine-2-carboxamide (example 113, 0.1 g, 250 μmol) in dry dichloromethane (2 ml) was added Dess-Martin periodinane (111 mg, 262 μmol). The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with dichloromethane and quenched with a 1.0M aqueous solution of sodium bicarbonate with 5% sodium thiosulfate. The bi-phasic mixture was stirred for 20 minutes and then transferred into a separatory funnel. The organic phase was dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a heptane/(solution of 3% Et3N in ethyl acetate) gradient to yield the title compound (71 mg, 71%). MS (ESI, m/z): 399.5 (M+H+).

Workup

  1. customquenched with a 1.0M aqueous solution of sodium bicarbonate with 5% sodium thiosulfate
  2. stirringThe bi-phasic mixture was stirred for 20 minutes
  3. customtransferred into a separatory funnel
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. customevaporated down to dryness
  6. customThe crude material was purified by flash chromatography on silica eluting with a heptane/(solution of 3% Et3N in ethyl acetate) gradient

Sources & evidence

ORD record
ord-367d97d4a6634cbd941c6e36519557a5
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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