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

HRID 732531Notes

Reaction equation

HRID 732531 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[C:5]1[CH:17]=[C:16]([CH:18]([CH:20]2[CH2:22][CH2:21]2)[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>>[CH2:1]([O:3][C:4](=[O:23])[C:5]1[CH:17]=[C:16]([C:18]([CH:20]2[CH2:22][CH2:21]2)=[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

3

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 688170545-(Cyclopropyl-hydroxymethyl)-N-methyl-N-propyl-isophthalamic acid ethyl ester

Product 1

HCID 688158375-Cyclopropanecarbonyl-N-methyl-N-propyl-isophthalamic acid ethyl ester

Procedure

Mix 5-(cyclopropyl-hydroxymethyl)-N-methyl-N-propyl-isophthalamic acid ethyl ester (122 mg, 0.38 mmol) and Dess-Martin periodinane (245 mg, 0.57) in CDCl3 (5 mL) and stir at room temperature for 2 h. Quench the reaction mixture with premixed sodium thiosulfate (500 mg) in 5% aqueous sodium carbonate solution (5 mL). Separate the organic layer and extract the aqueous layer with dichloromethane (2×5 mL). Combine organic layers and concentrate to give the title compound as a crude residue which is used in the next step without further purification.

Workup

  1. customQuench the reaction mixture with premixed sodium thiosulfate (500 mg) in 5% aqueous sodium carbonate solution (5 mL)
  2. customSeparate the organic layer
  3. extractionextract the aqueous layer with dichloromethane (2×5 mL)
  4. concentrationCombine organic layers and concentrate

Sources & evidence

ORD record
ord-a6eca464d1e949cca4e75336377a5dbb
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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