Triacetoxyperiodinane → 3(RS)-(tert-butoxyformamido)-5,5,5-trifluoro-2',4'-dimethyl-2-oxovaleranilide

HRID 635624Notes

Reaction equation

HRID 635624 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:23][C:24]([F:27])([F:26])[F:25])[CH:10]([OH:22])[C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=1[CH3:21])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>ClCCl>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:23][C:24]([F:25])([F:26])[F:27])[C:10](=[O:22])[C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=1[CH3:21])=[O:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 212589493(RS)-(tert-butoxyformamido)-5,5,5-trifluoro-2(RS)-hydroxy-2',4' dimethylvaleranilide

Product 1

HCID 212590433(RS)-(tert-butoxyformamido)-5,5,5-trifluoro-2',4'-dimethyl-2-oxovaleranilideYield 62.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 360 mg (0.92 mmol) of 3(RS)-(tert-butoxyformamido)-5,5,5-trifluoro-2(RS)-hydroxy-2′,4′-dimethylvaleranilide and 424 mg (1 mmol) of 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one in 10 ml of dichloromethane was stirred under a nitrogen atmosphere for 1 hour. The solution was extracted with a solution of 2.5 g of sodium thiosulphate in 10 ml of saturated sodium bicarbonate solution, then dried over anhydrous magnesium sulphate, filtered and evaporated to dryness. The residue was chromatographed on silica gel using 25% ethyl acetate in petroleum ether for the elution. The solid obtained was triturated with petroleum ether to give 222 mg of 3(RS)-(tert-butoxyformamido)-5,5,5-trifluoro-2′,4′-dimethyl-2-oxovaleranilide as a white solid, 1H NMR (250 MHz, CDCl3) δ:1.4 (s,9H), 2.25 (s,3H), 2.3 (s,3H), 2.8-3.1 (m,2H), 5.2-5.3 (m,1H), 5.4-5.5 (d,1H), 7.0-7.1 (m,2H), 7.7-7.8 (d,1H), 8.4-8.5 (br.s,1H).

Workup

  1. extractionThe solution was extracted with a solution of 2.5 g of sodium thiosulphate in 10 ml of saturated sodium bicarbonate solution
  2. dry with materialdried over anhydrous magnesium sulphate
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was chromatographed on silica gel using 25% ethyl acetate in petroleum ether for the elution
  6. customThe solid obtained
  7. customwas triturated with petroleum ether

Sources & evidence

ORD record
ord-745db6a612f1436baf453977c628f0e6
Source dataset
uspto-grants-2001_02
Patent number
US06187905B1

Reaction notes

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