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Hydrogen Peroxide → 4-(3-Carbamoylmethoxy-5-methoxy-benzoylamino)-piperidine-1-carboxylic acid tert-butyl ester

HRID 502459
Notes
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Reaction equation

HRID 502459 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:28])[C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH2:25][C:26]#[N:27])[CH:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-:30].[K+].[K+].OO>CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:28])[C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH2:25][C:26](=[O:30])[NH2:27])[CH:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 684560424-(3-Cyanomethoxy-5-methoxy-benzoylamino)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 684577954-(3-Carbamoylmethoxy-5-methoxy-benzoylamino)-piperidine-1-carboxylic acid tert-butyl esterYield 504.2%

Reagents, catalysts & solvents 1

HCID 679
Dimethyl Sulfoxide
Solvent

Procedure

2.10 g (5.4 mmol) of 4-(3-cyanomethoxy-5-methoxy-benzoylamino)-piperidine-1-carboxylic acid tert-butyl ester (example 245) and 0.15 g (1.1 mmol) of potassium carbonate were suspended under argon in 10 mL of DMSO at rt; while stirring, 0.93 mL (1.05 g=2.0 eq.) of hydrogen peroxide solution (35% in water) was added below 25° C. and stirring continued at ambient temperature for 24 hours. Then, the reaction mixture was poured into crashed ice and extracted three times with MeCl2 /2-propanol (4:1); the organic phases were evaporated i.V. to yield 2.26 g of the crude title compound as colorless solid. MS: 408.1 (MH+).

Workup

  1. stirringstirring
  2. additionThen, the reaction mixture was poured
  3. extractionextracted three times with MeCl2 /2-propanol (4:1)
  4. customthe organic phases were evaporated i.V

Sources & evidence

ORD record
ord-8168d9e9fd6f48d993ad2bcbe3fc10d5
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07772253B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes