Triacetoxyperiodinane → HCID 10099476, compound

HRID 349285Notes

Reaction equation

HRID 349285 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[F:23][C:24]([F:63])([F:62])[C:25]1[CH:26]=[C:27]([CH:55]=[C:56]([C:58]([F:61])([F:60])[F:59])[CH:57]=1)[CH2:28][N:29]1[C:33]([N:34]2[CH:38]=[CH:37][N:36]=[CH:35]2)=[C:32]([C:39]([C:41]2[C:42](CO)=[N:43][O:44][C:45]=2[C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=2[Cl:52])=[O:40])[N:31]=[N:30]1>ClCCl.CCOC(C)=O>[F:62][C:24]([F:23])([F:63])[C:25]1[CH:26]=[C:27]([CH:55]=[C:56]([C:58]([F:61])([F:60])[F:59])[CH:57]=1)[CH2:28][N:29]1[C:33]([N:34]2[CH:38]=[CH:37][N:36]=[CH:35]2)=[C:32]([C:39](=[O:40])[CH:41]([C:45](=[O:44])[C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=2[Cl:52])[C:42]#[N:43])[N:31]=[N:30]1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 9916663HCID 9916663, compound

Product 1

HCID 10099476HCID 10099476, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add Dess-Martin periodinane (1.5 g, 3.54 mmol) to a solution of [1-(3,5-Bis-trifluoromethyl-benzyl)-5-imidazol-1-yl-1H-[1,2,3]triazol-4-yl]-[5-(2-chloro-phenyl)-3-hydroxymethyl-isoxazol-4-yl]-methanone (0.7 g, 1.17 mmol) in dichloromethane (10.0 mL). Stir at RT for 4 h, dilute with EtOAc and wash with 2N NaOH, water and brine, then dry, filter, and concentrate. Recyrstallize crude material from dichloromethane to give the title compound. (0.10 g, 15%). MS [ES] 567.0 (M+H)+, 565.0 (M−H); 1H NMR (400 MHz, DMSO-d6) δ 8.04 (s, 1H), 7.70 (s, 2H), 7.69 (s, 1H), 7.25 (br s, 2H), 7.19 (m, 2H), 7.03 (s, 1H), 6.98 (m, 1H), 5.68 (s, 2H).

Workup

  1. washwash with 2N NaOH, water and brine
  2. customdry
  3. filtrationfilter
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-6d2c1e0b801145d482c3ecfd0863d231
Source dataset
uspto-grants-2007_02
Patent number
US07179804B2

Reaction notes

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