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Water → cis-N-(3-Methoxy-4-piperidinyl)-4-amino-5-chloro-2-((S)-1-methyl-2-butynyl)oxybenzamide

HRID 343424
Notes
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Reaction equation

HRID 343424 reaction equation
C(OC([N:6]1[CH2:11][CH2:10][C@H:9]([NH:12][C:13](=[O:28])[C:14]2[CH:19]=[C:18]([Cl:20])[C:17]([NH2:21])=[CH:16][C:15]=2[O:22][C@@H:23]([CH3:27])[C:24]#[C:25][CH3:26])[C@H:8]([O:29][CH3:30])[CH2:7]1)=O)C.[OH-].[K+].O>CC(O)C>[CH3:30][O:29][C@H:8]1[C@@H:9]([NH:12][C:13](=[O:28])[C:14]2[CH:19]=[C:18]([Cl:20])[C:17]([NH2:21])=[CH:16][C:15]=2[O:22][C@@H:23]([CH3:27])[C:24]#[C:25][CH3:26])[CH2:10][CH2:11][NH:6][CH2:7]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 69232225cis-N-(1-ethoxycarbonyl-3-methoxy-4-piperidinyl)-4-amino-5-chloro-2-((S)-1-methyl-2-butynyl)oxybenzamide

Product 1

HCID 69232145cis-N-(3-Methoxy-4-piperidinyl)-4-amino-5-chloro-2-((S)-1-methyl-2-butynyl)oxybenzamideYield 16.3%

Reagents, catalysts & solvents 1

HCID 3776
Isopropanol
Solvent

Procedure

2.50 g of the cis-N-(1-ethoxycarbonyl-3-methoxy-4-piperidinyl)-4-amino-5-chloro-2-((S)-1-methyl-2-butynyl)oxybenzamide prepared in the Example 7 and 4.5 g of potassium hydroxide were dissolved in 2-propanol. The obtained solution was refluxed for 1.5 hours and cooled, followed by the addition thereto of water. The resulting mixture was extracted with 10% 2-propanol/chloroform thrice. The combined organic phases were dried over magnesium sulfate and freed from the solvent. The residue was purified by silica gel column chromatography (5 to 12% methanol/dichloromethane) to give 0.34 g of the title compound.

Workup

  1. temperatureThe obtained solution was refluxed for 1.5 hours
  2. temperaturecooled
  3. additionfollowed by the addition
  4. extractionThe resulting mixture was extracted with 10% 2-propanol/chloroform thrice
  5. dry with materialThe combined organic phases were dried over magnesium sulfate
  6. customThe residue was purified by silica gel column chromatography (5 to 12% methanol/dichloromethane)

Sources & evidence

ORD record
ord-94d29bc620cc4577a7a3c7d8a43b375b
Source dataset
uspto-grants-1999_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05861418

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes