Hydrochloric Acid → N-(2,6-dichlorobenzoyl)-4-(6-methoxy-2-hydoxyphenyl)-L-phenylalanine ethyl ester

HRID 24675Notes

Reaction equation

HRID 24675 reaction equation
[CH2:1]([O:3][C:4](=[O:36])[C@H:5]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:29]([O:30]C)=[CH:28][CH:27]=[CH:26][C:25]=2[O:32][CH2:33]OC)=[CH:20][CH:19]=1)[NH:6][C:7](=[O:16])[C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:15])[CH3:2].Cl>CCO.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:36])[C@H:5]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:25]([O:32][CH3:33])=[CH:26][CH:27]=[CH:28][C:29]=2[OH:30])=[CH:20][CH:19]=1)[NH:6][C:7](=[O:16])[C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:15])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 54508489N-(2,6-dichlorobenzoyl)-4-(6-methoxy-2-methoxymethoxyphenyl)-L-phenylalanine ethyl ester

Product 1

HCID 54105918N-(2,6-dichlorobenzoyl)-4-(6-methoxy-2-hydoxyphenyl)-L-phenylalanine ethyl esterYield 92.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(2,6-dichlorobenzoyl)-4-(6-methoxy-2-methoxymethoxyphenyl)-L-phenylalanine ethyl ester (938 mg) in EtOH (25 mL) was added HCl (4 N in dioxane, 5 mL), and then the mixture was stirred under N2 for 4 h at room temperature. The mixture was diluted with AcOEt, washed with H2O and brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography (silica gel; eluent: AcOEt/hexane 1:2) to afford N-(2,6-dichlorobenzoyl)-4-(6-methoxy-2-hydoxyphenyl)-L-phenylalanine ethyl ester (795 mg). ESMS m/Z 488 (MH+), 486 (M−H)−.

Workup

  1. washwashed with H2O and brine
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by column chromatography (silica gel; eluent: AcOEt/hexane 1:2)

Sources & evidence

ORD record
ord-beaf8466342a450e94f713ac43f43d89
Source dataset
uspto-grants-2005_02
Patent number
US06855843B2

Reaction notes

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