Triacetoxyperiodinane → HCID 59129263, compound

HRID 1847511Notes

Reaction equation

HRID 1847511 reaction equation
[C:1]([C:5]1[N:6]([CH2:31][CH:32]([OH:35])[CH2:33][OH:34])[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([NH:14][C:15]([C:17]1([C:20]3[CH:30]=[CH:29][C:23]4[O:24][C:25]([F:28])([F:27])[O:26][C:22]=4[CH:21]=3)[CH2:19][CH2:18]1)=[O:16])=[CH:9][CH:8]=2)([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=[O:38]>CS(C)=O>[C:1]([C:5]1[N:6]([CH2:31][C:32](=[O:35])[C:33]([OH:38])=[O:34])[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([NH:14][C:15]([C:17]1([C:20]3[CH:30]=[CH:29][C:23]4[O:24][C:25]([F:28])([F:27])[O:26][C:22]=4[CH:21]=3)[CH2:18][CH2:19]1)=[O:16])=[CH:9][CH:8]=2)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 59129446HCID 59129446, compound

Product 1

HCID 59129263HCID 59129263, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of N-(2-tert-butyl-1-(2,3-dihydroxypropyl)-1H-indol-5-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropane-carboxamide (97 mg, 0.20 mmol) in DMSO (1 mL) was added Dess-Martin periodinane (130 mg, 0.30 mmol). The mixture was stirred at room temperature for 3 h. The solid was filtered off and washed with EtOAc. The filtrate was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc twice and the combined organic layers were washed with brine and dried over MgSO4. After the removal of solvent, the residue was purified by preparative TLC to yield 3-(2-tert-butyl-5-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-1H-indol-1-yl)-2-oxopropanoic acid that was used without further purification.

Workup

  1. filtrationThe solid was filtered off
  2. washwashed with EtOAc
  3. customThe filtrate was partitioned between EtOAc and water
  4. extractionThe aqueous layer was extracted with EtOAc twice
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. customAfter the removal of solvent
  8. customthe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-5aca6936ae3442c4a8365d89971be1b7
Source dataset
uspto-grants-2015_02
Patent number
US08952050B2

Reaction notes

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