Triacetoxyperiodinane → HCID 67970698, compound

HRID 1184385Notes

Reaction equation

HRID 1184385 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([O:24][CH2:25][CH:26]3[CH2:28][CH2:27]3)=[N:10][CH:11]=[C:12]([CH:23]=2)[C:13]([NH:15][C@H:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]2[OH:22])=[O:14])=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([O:24][CH2:25][CH:26]3[CH2:27][CH2:28]3)=[N:10][CH:11]=[C:12]([CH:23]=2)[C:13]([NH:15][C@H:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C:17]2=[O:22])=[O:14])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67970610HCID 67970610, compound

Product 1

HCID 67970698HCID 67970698, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1.651 g 5-(4-chloro-phenyl)-6-cyclopropylmethoxy-N-((1S,2R)-2-hydroxy-cyclohexyl)-nicotinamide in 25 ml methylene chloride, was added 2.62 g Dess-Martin periodinane as 15% solution in dichloromethane. The reaction mixture was stirred at room temperature for 18 h. The solvent was evaporated and the residue was purified by chromatography on silica gel using a gradient of heptane:ethyl acetate=95:5 to 40:60 to yield 1.46 g of the title compound as white foam. MS (EI): 399.1 (M+H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by chromatography on silica gel using a gradient of heptane

Sources & evidence

ORD record
ord-2f3afb0a36894dc39c264d2b617a2056
Source dataset
uspto-grants-2014_03
Patent number
US08669254B2

Reaction notes

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