Triacetoxyperiodinane → HCID 59129263, compound

HRID 2038054Notes

Reaction equation

HRID 2038054 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-c8215d3f344f4334bfc13315754bc3fd
Source dataset
uspto-grants-2013_11
Patent number
US08575209B2

Reaction notes

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