Triacetoxyperiodinane → HCID 86590604, compound

HRID 1824445Notes

Reaction equation

HRID 1824445 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH2:24][CH:25]([NH:34][C:35]([CH:37]1[N:41]2[C:42](=[O:61])[CH:43]([NH:48][C:49]([C:51]3[CH:60]=[CH:59][C:58]4[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=4)[CH:52]=3)=[O:50])[CH2:44][CH:45]=[CH:46][CH2:47][CH:40]2[CH2:39][CH2:38]1)=[O:36])[CH2:26][C:27]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])=[O:28].C([O-])(O)=O.[Na+]>C(Cl)Cl>[OH:23][CH:24]1[CH:25]([NH:34][C:35]([CH:37]2[N:41]3[C:42](=[O:61])[CH:43]([NH:48][C:49]([C:51]4[CH:60]=[CH:59][C:58]5[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=5)[CH:52]=4)=[O:50])[CH2:44][CH:45]=[CH:46][CH2:47][CH:40]3[CH2:39][CH2:38]2)=[O:36])[CH2:26][C:27](=[O:28])[N:29]1[S:30]([CH3:33])(=[O:31])=[O:32]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 86590602HCID 86590602, compound

Product 1

HCID 86590604HCID 86590604, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin reagent (90 mg, 0.21 mmol) is added to an ice cold solution of 6-[(Naphthalene-2-carbonyl)-amino]-5-oxo-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carboxylic acid (1-hydroxymethyl-3-methanesulfonylamino-3-oxo-propyl)-amide (48 mg, 0.09 mmol) in CH2Cl2 (5 mL). The solution is stirred at 0 C. for 2 h and treated with saturated NaHCO3. The resulting solution is extracted with EtOAc and the combined organic extracts are washed with brine, dried (Na2SO4), filtered, and concentrated. The crude residue obtained is purified by flash chromatography on silica gel (CH2Cl2/MeOH) to yield 27 mg of product as a mixture of diastereomers. MS (ESI) 555 (M+1).

Workup

  1. extractionThe resulting solution is extracted with EtOAc
  2. washthe combined organic extracts are washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue obtained
  7. customis purified by flash chromatography on silica gel (CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-b49f945b46c64320ba96a0ff5fce2457
Source dataset
uspto-grants-2006_05
Patent number
US07041696B2

Reaction notes

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