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

HRID 635624노트

반응식

HRID 635624 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-745db6a612f1436baf453977c628f0e6
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06187905B1

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