Triacetoxyperiodinane → HCID 57436939, compound

HRID 1713628Notes

Reaction equation

HRID 1713628 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH:24]([C:30]1[CH:35]=[CH:34][C:33]([N:36]2[CH:40]([CH2:41][CH2:42][CH2:43][C:44]3[S:48][C:47]([C:49]([O:51][CH:52]([CH3:54])[CH3:53])=[O:50])=[CH:46][CH:45]=3)[C:39](=[O:55])[NH:38][C:37]2=[O:56])=[CH:32][CH:31]=1)[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>C(Cl)Cl>[C:24]([C:30]1[CH:35]=[CH:34][C:33]([N:36]2[CH:40]([CH2:41][CH2:42][CH2:43][C:44]3[S:48][C:47]([C:49]([O:51][CH:52]([CH3:53])[CH3:54])=[O:50])=[CH:46][CH:45]=3)[C:39](=[O:55])[NH:38][C:37]2=[O:56])=[CH:32][CH:31]=1)(=[O:23])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 24748704HCID 24748704, compound

Product 1

HCID 57436939HCID 57436939, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (9 mg, 0.021 mmol) was added to a solution of 31 (9 mg, 0.016 mmol) in CH2Cl2 (0.16 mL) at room temperature. After 4 h the reaction mixture was diluted with 20% EtOAc/hexanes (2 mL) and filtered through celite, washing with additional 20% EtOAc/hexanes (2 mL). The filtrate was concentrated in vacuo. The crude residue was purified on 4 g silica (hexanes→EtOAc, gradient) to afford 4.5 mg (56%) of the title compound (32).

Workup

  1. filtrationfiltered through celite
  2. washwashing with additional 20% EtOAc/hexanes (2 mL)
  3. concentrationThe filtrate was concentrated in vacuo
  4. customThe crude residue was purified on 4 g silica (hexanes→EtOAc, gradient)

Sources & evidence

ORD record
ord-a3b1ecb6fbfe4e7f9d9fa96c2b57d470
Source dataset
uspto-grants-2010_09
Patent number
US07795287B2

Reaction notes

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