HCID 57971724, compound → HCID 57971709, compound

HRID 2276988Notes

Reaction equation

HRID 2276988 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-8527cae9a506456f959594cd4442fc0e
Source dataset
uspto-grants-2015_09
Patent number
US09133104B2

Reaction notes

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