Hydrochloric Acid → HCID 12109165, compound

HRID 619255Notes

Reaction equation

HRID 619255 reaction equation
N[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C@H:12]([NH:14][C:15](=[O:17])[CH3:16])[CH3:13])[C:5]([O:7][CH3:8])=[O:6].N([O-])=O.[Na+].[ClH:22]>C(O)(=O)C.S(=O)(=O)(O)O.[Cu]Cl>[C:15]([NH:14][C@@H:12]([C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[Cl:22])[CH3:13])(=[O:17])[CH3:16]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 12109152HCID 12109152, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 12109165HCID 12109165, compound

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of methyl (R)-3-amino-4-(1-acetamidoethyl)benzoate (600 mg) in acetic acid (6 ml) was dropwise added to a solution of sodium nitrite (193 mg) in conc. sulfuric acid (2 ml) at room temperature, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was dropwise added to a solution of copper(I) chloride (550 mg) in conc. hydrochloric acid (6 ml) under ice-cooling, and the mixture was stirred at room temperature for 5 hours. After the reaction, the reaction mixture was poured into ice water, and extracted with chloroform. The extract was washed with water, dried, and concentrated. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=30:1) to give 460 mg of methyl (R)-4-(1-acetamidoethyl)-3-chlorobenzoate.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 5 hours
  3. customAfter the reaction
  4. extractionextracted with chloroform
  5. washThe extract was washed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-32be6beddeb04c579cb56367bb999264
Source dataset
uspto-grants-1999_09
Patent number
US05958944

Reaction notes

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