Hydrochloric Acid → HCID 53636182, compound

HRID 1060439Notes

Reaction equation

HRID 1060439 reaction equation
[CH3:1][O:2][C:3](=[O:37])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:28]([O:29][CH3:30])=[CH:27][CH:26]=[C:25]([O:31]COC)[C:24]=2[O:35][CH3:36])=[CH:19][CH:18]=1)[NH:5][C:6](=[O:15])[C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:14].Cl>CO.O1CCOCC1>[CH3:1][O:2][C:3](=[O:37])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:28]([O:29][CH3:30])=[CH:27][CH:26]=[C:25]([OH:31])[C:24]=2[O:35][CH3:36])=[CH:19][CH:18]=1)[NH:5][C:6](=[O:15])[C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:14]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 53989823HCID 53989823, compound

Product 1

HCID 53636182HCID 53636182, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

N-(2,6-Dichlorobenzoyl)-4-(2,6-dimethoxy-3methoxymethoxyphenyl)-L-phenylalanine methyl ester (165 mg) was dissolved in MeOH (5 mL) and HCl in dioxane (4 M, 1 mL) was added to the mixture. The mixture was stirred at room temperature for 3 h. The mixture was evaporated and the residue was taken up with water (40 mL) and extracted with CH2Cl2. The extract was dried (MgSO4), filtered and evaporated. The residue was purified by preparative TLC (silica gel; eluent: hexane and AcOEt 3:1 to 1:1) to give N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxy-3-hydroxyphenyl)-L-phenylalanine methyl ester (145 mg ).

Workup

  1. customThe mixture was evaporated
  2. extractionextracted with CH2Cl2
  3. dry with materialThe extract was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by preparative TLC (silica gel; eluent: hexane and AcOEt 3:1 to 1:1)

Sources & evidence

ORD record
ord-c8e503bc06a540a494f3b0067e0502ea
Source dataset
uspto-grants-2003_02
Patent number
US06521666B1

Reaction notes

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