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Water → methyl 2-(4-chloro-3-((2-chloro-4-(((2S)-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-2-yl)methoxy)benzoyl)amino)phenyl)-2-methylpropanoate

HRID 1818689
Notes
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Reaction equation

HRID 1818689 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([O:11][CH2:12][C@@H:13]2[CH2:18][N:17]([CH3:19])[C:16]3[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=3[O:14]2)[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[NH2:24][C:25]1[CH:26]=[C:27]([C:32]([CH3:38])([CH3:37])[C:33]([O:35][CH3:36])=[O:34])[CH:28]=[CH:29][C:30]=1[Cl:31].N1C=CC=CC=1.O>ClCCl>[Cl:31][C:30]1[CH:29]=[CH:28][C:27]([C:32]([CH3:37])([CH3:38])[C:33]([O:35][CH3:36])=[O:34])=[CH:26][C:25]=1[NH:24][C:4](=[O:5])[C:3]1[CH:7]=[CH:8][C:9]([O:11][CH2:12][C@@H:13]2[CH2:18][N:17]([CH3:19])[C:16]3[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=3[O:14]2)=[CH:10][C:2]=1[Cl:1]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 23125543HCID 23125543, compoundHCID 86609826HCID 86609826, compound

Product 1

HCID 66782455methyl 2-(4-chloro-3-((2-chloro-4-(((2S)-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-2-yl)methoxy)benzoyl)amino)phenyl)-2-methylpropanoate

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Procedure

A solution of the compound prepared in Example 17 in dichloromethane (1.8 mL) was dropped to a solution of the compound (100 mg) prepared in Example 16 in dichloromethane (1.8 mL). Pyridine (0.057 mL) was added to the reaction mixture, which was stirred for 1 hour at room temperature. The reaction mixture dissolved to water was extracted with ethyl acetate. The organic layer was sequentially washed with diluted hydrochloric acid, saturated sodium hydrogencarbonate solution, and saturated brine solution and was dried by anhydrous magnesium sulphate. The title compound (164 mg) having the following physical data was obtained by purifying the residue obtained by removing the solvent by silica gel column chromatography (n-hexane:ethyl acetate=4:1). TLC: Rf 0.41 (n-hexane:ethyl acetate=2:1).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was sequentially washed with diluted hydrochloric acid, saturated sodium hydrogencarbonate solution, and saturated brine solution
  3. dry with materialwas dried by anhydrous magnesium sulphate
  4. customwas obtained
  5. customby purifying the residue
  6. customobtained
  7. customby removing the solvent by silica gel column chromatography (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-7c0d61b17cb24852a8481931318f38b2
Source dataset
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07601712B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes