Triacetoxyperiodinane → HCID 86635931, compound

HRID 561866Notes

Reaction equation

HRID 561866 reaction equation
[Cl:1][C:2]1[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][O:41][CH3:42])=[CH:35][C:3]=1[CH2:4][N:5]([CH:32]1[CH2:34][CH2:33]1)[C:6](=[O:31])[CH:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][O:21][C:22]2[C:27]([Cl:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=2[Cl:30])=[CH:14][CH:13]=1)[CH:8]([OH:10])[CH3:9].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[Cl:1][C:2]1[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][O:41][CH3:42])=[CH:35][C:3]=1[CH2:4][N:5]([CH:32]1[CH2:34][CH2:33]1)[C:6](=[O:31])[CH:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][O:21][C:22]2[C:27]([Cl:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=2[Cl:30])=[CH:14][CH:13]=1)[C:8](=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 66761782HCID 66761782, compound

Product 1

HCID 86635931HCID 86635931, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[2-Chloro-5-(2-methoxyethyl)benzyl]-N-cyclopropyl-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-3-hydroxybutanamide from the previous step (1 eq.) in dichloromethane (0.05 M) was added at 0° C. Dess-Martin periodinane (1.2 eq.). The resulting solution was allowed to warm to RT over 2 h before the reaction was quenched with methanol and diluted with ether. This was then washed sequentially with sat. aq. NaHCO3, water and brine. Drying of the organic layer over MgSO4, filtration and concentration of the filtrate in vacuo afforded the crude product as a colorless oil. Further purification by way of flash chromatography (SiO2, Hex→10:1 (v/v) Hex:EtOAc) afforded the title compound as a viscous oil.

Workup

  1. customwas quenched with methanol
  2. additiondiluted with ether
  3. washThis was then washed sequentially with sat. aq. NaHCO3, water and brine
  4. dry with materialDrying of the organic layer over MgSO4, filtration and concentration of the filtrate in vacuo
  5. customafforded the crude product as a colorless oil
  6. customFurther purification by way of flash chromatography (SiO2, Hex→10:1 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-928d51b94df04ab8a1aeb0bac8a2a4a0
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

Loading…