Triacetoxyperiodinane → 5-Acetyl-N-methyl-N-propyl-isophthalamic acid ethyl ester

HRID 732566Notes

Reaction equation

HRID 732566 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:17]=[C:16]([CH:18]([OH:20])[CH3:19])[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:21])[C:5]1[CH:17]=[C:16]([C:18](=[O:20])[CH3:19])[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 688153185-(1-Hydroxyethyl)-N-methyl-N-propyl-isophthalamic acid ethyl ester

Product 1

HCID 688169505-Acetyl-N-methyl-N-propyl-isophthalamic acid ethyl esterYield 79.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Treat a solution of 5-(1-hydroxyethyl)-N-methyl-N-propyl-isophthalamic acid ethyl ester (250 mg, 0.85 mmol) in dichloromethane (10 mL) with Dess-Martin periodinane (470 mg, 1.11 mmol). Stir at room temperature for 2.5 h, quench with 10% aqueous sodium sulfate, extract with ethyl acetate (50 mL). Wash with 10% aqueous sodium sulfate solution, saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 50:50 ethyl acetate:hexanes) to give the title compound (196 mg, 78%).

Workup

  1. customquench with 10% aqueous sodium sulfate
  2. extractionextract with ethyl acetate (50 mL)
  3. washWash with 10% aqueous sodium sulfate solution, saturated aqueous sodium chloride
  4. dry with materialdry (magnesium sulfate)
  5. concentrationconcentrate
  6. custompurify
  7. wash(silica gel chromatography, eluting with 50:50 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-ebe2a111a0b449c4b45f826950947742
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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