Triacetoxyperiodinane → HCID 25008286, compound

HRID 2217778Notes

Reaction equation

HRID 2217778 reaction equation
[OH:1][CH2:2][C:3]([C:6]1[S:10][C:9]([NH:11][C:12](=[O:29])[CH:13]([NH:17][C:18](=[O:28])[CH2:19][C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[C:22]([F:27])[CH:21]=2)[CH2:14][CH2:15][CH3:16])=[N:8][N:7]=1)([CH3:5])[CH3:4].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:4][C:3]([C:6]1[S:10][C:9]([NH:11][C:12](=[O:29])[CH:13]([NH:17][C:18](=[O:28])[CH2:19][C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[C:22]([F:27])[CH:21]=2)[CH2:14][CH2:15][CH3:16])=[N:8][N:7]=1)([CH3:5])[CH:2]=[O:1]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86596684HCID 86596684, compound

Product 1

HCID 25008286HCID 25008286, compoundYield 5.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-[2-(3,5-difluoro-phenyl)-acetylamino]-pentanoic acid [5-(2-hydroxy-1,1-dimethyl-ethyl)-[1,3,4]thiadiazol-2-yl]-amide (40 mg, 0.93 mmol) and Dess-Martin periodinane (1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one) (90 mg) in methylene chloride (3 ml) was stirred at rt for 3 hr. The mixture was quenched with water, methylene chloride and filtered through celite. The filtrate was transferred to separatory funnel and the organic layer was separated, dried and concentrated to give 42 mg of crude material. The crude material was purified by silica gel column chromatography using methylene chloride to 1% methanol in methylene chloride as eluent to give 20 mg of the title compound as a tan glass solid. APCI M+1=425.2.

Workup

  1. customThe mixture was quenched with water, methylene chloride
  2. filtrationfiltered through celite
  3. customThe filtrate was transferred to separatory funnel
  4. customthe organic layer was separated
  5. customdried
  6. concentrationconcentrated
  7. customto give 42 mg of crude material
  8. customThe crude material was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9a8d30fed134459d9f873bf9c461cce7
Source dataset
uspto-grants-2008_08
Patent number
US07408068B2

Reaction notes

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