Triacetoxyperiodinane → HCID 86615013, compound

HRID 1436671Notes

Reaction equation

HRID 1436671 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:17]=[C:16]([CH2:18][OH:19])[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=1)[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:17]=[C:16]([CH:18]=[O:19])[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=1)[CH3:2]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 688164795-hydroxymethyl-N-methyl-N-propyl-isophthalamic acid ethyl ester

Product 1

HCID 86615013HCID 86615013, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Mix 5-hydroxymethyl-N-methyl-N-propyl-isophthalamic acid ethyl ester (2.8 g, 10 mmol) and Dess-Martin periodinane (5.1 g, 12 mmol) in dichloromethane (50 mL) in an ice-bath. Stir the mixture overnight at room temperature. Dilute with dichloromethane (50 mL) and quench it with premixed sodium thiosulfate (1.5 g) in 5% aqueous sodium bicarbonate solution (50 mL). Filter the slurry through a filtering agent and separate the organic layer. Dry (sodium sulfate), concentrate and purify (silica gel chromatography, eluting with 50:50 ethyl acetate:hexanes) to give the title compound (2.2 g, 79%).

Workup

  1. customquench it with premixed sodium thiosulfate (1.5 g) in 5% aqueous sodium bicarbonate solution (50 mL)
  2. filtrationFilter the slurry through a filtering agent
  3. customseparate the organic layer
  4. dry with materialDry (sodium sulfate)
  5. concentrationconcentrate
  6. custompurify
  7. wash(silica gel chromatography, eluting with 50:50 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-3572410bb7334cb39480b2d875730e69
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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