Triacetoxyperiodinane → HCID 118236058, compound

HRID 1481279Notes

Reaction equation

HRID 1481279 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C@H:8]([OH:51])[CH2:9][CH2:10][N:11]([C@@H:23]2[C:40]3=[CH:41][C:36](=[CH:37][C:38]([O:42][CH3:43])=[N:39]3)[C:35]3[C:30](=[CH:31][C:32]([NH:44][C:45](=[O:48])[O:46][CH3:47])=[CH:33][CH:34]=3)[NH:29][C:28](=[O:49])[C@H:27]([CH3:50])[CH2:26][CH2:25][CH2:24]2)[C:12](=[O:22])[CH2:13][P:14]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])=[O:15])[C:3]=1[F:52].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8](=[O:51])[CH2:9][CH2:10][N:11]([C@@H:23]2[C:40]3=[CH:41][C:36](=[CH:37][C:38]([O:42][CH3:43])=[N:39]3)[C:35]3[C:30](=[CH:31][C:32]([NH:44][C:45](=[O:48])[O:46][CH3:47])=[CH:33][CH:34]=3)[NH:29][C:28](=[O:49])[C@H:27]([CH3:50])[CH2:26][CH2:25][CH2:24]2)[C:12](=[O:22])[CH2:13][P:14]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])=[O:15])[C:3]=1[F:52]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 118236117HCID 118236117, compound

Product 1

HCID 118236058HCID 118236058, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5P (15.5 mg, 0.020 mmol) in anhydrous DCM (4 mL) was added Dess-Martin periodinane (11.18 mg, 0.026 mmol). The mixture was stirred at ambient temperature for 1 h. The reaction mixture was diluted with water and extracted with DCM (3×). The combined organic layer was washed with brine, dried (Na2SO4), filtered, and evaporated to give 5Q (15 mg, 99%). MS (ESI) m/z: 762.0 (M+H)+.

Workup

  1. extractionextracted with DCM (3×)
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-05ec2a4526804ce4a97a2033105aadd7
Source dataset
uspto-grants-2016_08
Patent number
US09409908B2

Reaction notes

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