HCID 57971724, compound → HCID 57971709, compound

HRID 2360643Notes

Reaction equation

HRID 2360643 reaction equation
[CH2:1]([O:5][CH:6]([O:8][NH:9][C:10](=[O:28])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][OH:27])=[CH:22][CH:21]=1)=[O:18])[CH3:7])[CH:2]([CH3:4])[CH3:3]>C(Cl)Cl.O=[Mn]=O>[CH2:1]([O:5][CH:6]([O:8][NH:9][C:10](=[O:28])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([NH:19][C:20]1[CH:21]=[CH:22][C:23]([CH:26]=[O:27])=[CH:24][CH:25]=1)=[O:18])[CH3:7])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 57971724HCID 57971724, compound

Product 1

HCID 57971709HCID 57971709, compoundYield 801%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

Octanedioic acid (4-hydroxymethyl-phenyl)-amide (1-isobutoxyethoxy)-amide (100 mg, 0.025 mmol, 1.0 eq) was dissolved in DCM (5 mL). To the reaction mixture, was added MnO2 (286 mg, 0.33 mmol, 13.0 eq) and was stirred at room temperature for 1.5 h. The reaction mixture was filtered over Celite and washed through with DCM, followed by evaporation of solvent to give a yellow oil (78.6 mg, 79% yield) LCMS purity 53%, m/z 415 [M++Na]+. The product was used in the subsequent steps without further purification.

Workup

  1. filtrationThe reaction mixture was filtered over Celite
  2. washwashed through with DCM
  3. customfollowed by evaporation of solvent

Sources & evidence

ORD record
ord-24926bf8e98442cab8c23b649237a8cc
Source dataset
uspto-grants-2014_04
Patent number
US08686032B2

Reaction notes

Loading…