Triacetoxyperiodinane → HCID 86694563, compound

HRID 1426392Notes

Reaction equation

HRID 1426392 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([O:27][C:28]([NH:30][C@@H:31]([C@H:47]([O:56][Si:57]([C:60]([CH3:63])([CH3:62])[CH3:61])([CH3:59])[CH3:58])[CH2:48][O:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[CH2:32][CH2:33][CH:34]([OH:46])[CH2:35][C:36]1[CH:45]=[CH:44][C:39]([C:40]([O:42][CH3:43])=[O:41])=[CH:38][CH:37]=1)=[O:29])([CH3:26])([CH3:25])[CH3:24]>C(Cl)Cl>[C:23]([O:27][C:28]([NH:30][C@@H:31]([C@H:47]([O:56][Si:57]([C:60]([CH3:63])([CH3:62])[CH3:61])([CH3:58])[CH3:59])[CH2:48][O:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[CH2:32][CH2:33][C:34](=[O:46])[CH2:35][C:36]1[CH:37]=[CH:38][C:39]([C:40]([O:42][CH3:43])=[O:41])=[CH:44][CH:45]=1)=[O:29])([CH3:25])([CH3:24])[CH3:26]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86694561HCID 86694561, compound

Product 1

HCID 86694563HCID 86694563, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dess-martin reagent (390 mg, 0.92 mM) was placed in a 100 ml round bottom flask and 5 ml of methylene chloride was added, 5 min later, methyl 4-{(5R,6S)-5-[(tert-butoxycarbonyl)amino]-6-{[tert-butyl(dimethyl)silyl]oxy}-2-hydroxy-7-phenoxyheptyl}benzoate from step E (360 mg, 0.61 mM) in 5 ml of methylene chloride was added, and the resulting mixture was stirred for 3 h at RT. The mixture was then filtered and the filtrate was washed by saturated aqueous sodium bicarbonate solution, dried over sodium sulfate and concentrated to dryness. The residue was then loaded onto a Biotage column (40 S) and eluted with hexane/ethyl acetate (0-30% EA, 500 ml; 30-50% EA, 300 ml) to afford 139 mg of the title compound. LC-MS: m/z (ES) 608.24 (M=23).

Workup

  1. filtrationThe mixture was then filtered
  2. washthe filtrate was washed by saturated aqueous sodium bicarbonate solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness
  5. washeluted with hexane/ethyl acetate (0-30% EA, 500 ml; 30-50% EA, 300 ml)

Sources & evidence

ORD record
ord-a3187d5982d94bfba35bc2077d90f65f
Source dataset
uspto-grants-2015_01
Patent number
US08933102B2

Reaction notes

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