Triacetoxyperiodinane → HCID 86586179, compound

HRID 429389Notes

Reaction equation

HRID 429389 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][N:3]1[CH:12]([CH:25]([OH:37])[CH2:26][NH:27][S:28]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)(=[O:30])=[O:29])[CH:13]([NH:21][C:22]([CH3:24])=[O:23])[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>ClCCl.CCOCC>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][N:3]1[CH:12]([C:25](=[O:37])[CH2:26][NH:27][S:28]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)(=[O:30])=[O:29])[CH:13]([NH:21][C:22]([CH3:24])=[O:23])[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86586180HCID 86586180, compound

Product 1

HCID 86586179HCID 86586179, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To 3-(1,2,3,4-tetrahydro-1-oxo-isoquinoline-2-yl)-acetamino-5-benzenesulfonylamino-4-hydroxy-pentanoic acid, tert-butyl ester (0.9 g, 1.7 mMol) in 20 mL of dichloromethane was added 1.1.1-triacetoxy-1.1-dihydro-1.2-benziodoxol-3-(1H)-one (Dess Martin periodinane, 1.08 g, 2.5 mMol). After 2 hours at room temperature the reaction mixture was diluted with ether, filtered, washed with sodium hydrogen carbonate and water, dried over sodium sulfate, and concentrated under reduced pressure. Chromatography over silica (elution with dichloromethane/methanol 15:1) gave 3-(1,2,3,4-tetrahydro-1-oxo-isoquinoline-2-yl)-acetamino-5-benzenesulfonylamino-4-oxo-pentanoic acid, tert-butyl ester (0.45 g).

Workup

  1. filtrationfiltered
  2. washwashed with sodium hydrogen carbonate and water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c7d529ccf7fc4ec09e431d3bff3960c3
Source dataset
uspto-grants-2001_11
Patent number
US06316415B1

Reaction notes

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