HCID 53904716, compound → HCID 54138363, compound

HRID 1274192Notes

Reaction equation

HRID 1274192 reaction equation
C([NH:4][C@@H:5]([C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13]C)=[O:12])=[CH:9][C:8]=1[N:17]=[N+:18]=[N-:19])[CH3:6])(=O)C>Cl>[N:17]([C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:7]=1[C@H:5]([NH2:4])[CH3:6])[C:11]([OH:13])=[O:12])=[N+:18]=[N-:19]

Participants

3

Reactant 1

HCID 53904716HCID 53904716, compound

Product 1

HCID 54138363HCID 54138363, compoundYield 135.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of methyl (R)-4-(1-acetylaminoethyl)-3-azidobenzoate (1.6 g) in 2N hydrochloric acid (25 ml) was refluxed under heating for 8 hours. After the reaction, the mixture was concentrated under reduced pressure, and boiled with toluene to give crude (R)-3-azido-4-(1-aminoethyl)benzoic acid (1.7 g). Then, the mixture was added to a solution of sodium hydroxide (0.85 g) in water (25 ml). Benzyloxycarbonyl chloride (1.56 g) was dropwise added, and the mixture was stirred at room temperature for 5 hours. After the reaction, the solution was adjusted to have pH 4 with conc. hydrochloric acid. The mixture was extracted with chloroform, washed with water, and dried. The solvent was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=30:1) to give 1.6 g of pale-yellow (R)-3-azido-4-(1-benzyloxycarbonylaminoethyl)benzoic acid.

Workup

  1. temperatureunder heating for 8 hours
  2. customAfter the reaction
  3. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-39113060856245fda46d5f9a41d309ab
Source dataset
uspto-grants-2000_12
Patent number
US06156766

Reaction notes

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