Triacetoxyperiodinane → HCID 25008473, compound

HRID 2093200Notes

Reaction equation

HRID 2093200 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[F:23][C:24]([F:71])([F:70])[C:25]1[CH:26]=[C:27]([C@H:35]2[O:39][C:38](=[O:40])[N:37]([CH2:41][C:42]3[CH:47]=[C:46]([C:48]([F:51])([F:50])[F:49])[CH:45]=[CH:44][C:43]=3[C:52]3[C:57]([Cl:58])=[CH:56][CH:55]=[C:54]([C:59]4[CH:64]=[CH:63][C:62]([CH:65]([OH:67])[CH3:66])=[CH:61][C:60]=4[CH3:68])[CH:53]=3)[C@H:36]2[CH3:69])[CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1.CCOC(C)=O.CCCCCC>C(Cl)Cl>[C:65]([C:62]1[CH:63]=[CH:64][C:59]([C:54]2[CH:53]=[C:52]([C:43]3[CH:44]=[CH:45][C:46]([C:48]([F:49])([F:50])[F:51])=[CH:47][C:42]=3[CH2:41][N:37]3[C@@H:36]([CH3:69])[C@@H:35]([C:27]4[CH:26]=[C:25]([C:24]([F:71])([F:70])[F:23])[CH:30]=[C:29]([C:31]([F:33])([F:34])[F:32])[CH:28]=4)[O:39][C:38]3=[O:40])[C:57]([Cl:58])=[CH:56][CH:55]=2)=[C:60]([CH3:68])[CH:61]=1)(=[O:67])[CH3:66]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 21226206Ethyl acetate hexaneHCID 25008471HCID 25008471, compound

Product 1

HCID 25008473HCID 25008473, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin Periodinane (58.3 mg, 0.137 mmol) was added to a solution of alcohol from Example 51 (82 mg, 0.115 mmol) in methylene chloride (5 ml) at room temperature. The resulting slurry was stirred at room temperature for 1 h. No starting material was seen by TLC (EtOAc/hexane 2:8). The solid was filtered. The filtrate was concentrated. The residue was purified by flash column on silica gel, eluting with EtOAc/hexane (20:80) to give the title compound as a colorless solid. 1H NMR (CDCl3, 500 MHz): δ a mixture of 1:1 atopoisomers 7.90 (s, 1H), 7.89 (s, 1H), 7.84 (d, J=8 Hz, 1H), 7.72 (m, 4H), 7.62 (d, J=8.5 Hz, 1H), 7.51 (d, J=8.0 Hz, 0.5H), 7.46 (d, J=8.0 Hz, 0.5H), 7.40-7.34 (m, 2H), 7.26 (d, J=2.5 Hz, 0.5H), 7.21 (d, J=2.5 Hz, 0.5H), 5.62 (d, J=8.0 Hz, 1H), 5.02 (d, J=15.5 Hz, 0.5H), 4.83 (d, J=16.0 Hz, 0.5H), 4.08 (d, J=16.0 Hz, 0.5H), 4.01 (d, J=15.5 Hz, 0.5H), 3.99 (m, 0.5H), 3.90(m, 0.5H), 2.64 (s, 3H), 2.40 (s, 1.5H), 2.39 (s, 1.5H), 0.64 (d, J=6.5 Hz, 1.5H), 0.62 (d, J=6.5 Hz, 1.5H). LC/MS M+714.01.

Workup

  1. filtrationThe solid was filtered
  2. concentrationThe filtrate was concentrated
  3. customThe residue was purified by flash column on silica gel
  4. washeluting with EtOAc/hexane (20:80)

Sources & evidence

ORD record
ord-6a6a6a8cda264d14903571f1a9004fd0
Source dataset
uspto-grants-2013_05
Patent number
US08440702B2

Reaction notes

Loading…