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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1875563Generated: October 30, 2026

Benzoic acid, 2-amino-5-iodo- → 4-[(2-amino-5-iodobenzoyl)amino]-N-(2,6-dichlorobenzoyl)-L-phenylalanine isopropylester

https://huagongshe.com/reaction/1875563

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBenzoic acid, 2-amino-5-iodo-HCID 72911—
Reactant1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2723939—
Reactant1-Hydroxybenzotriazole hydrateHCID 2796029—
Reactant4-Amino-N-(2,6-dichlorobenzoyl)-L-phenylalanine IsopropylesterHCID 58018318—
SolventDimethylformamideHCID 6228—
SolventEthyl AcetateHCID 8857—
Product4-[(2-amino-5-iodobenzoyl)amino]-N-(2,6-dichlorobenzoyl)-L-phenylalanine isopropylesterHCID 86600885—

Reaction Conditions

Temperature0 °C

Reaction Steps

4-Amino-N-(2,6-dichlorobenzoyl)-L-phenylalanine Isopropylester, 1-hydroxybenzotriazole monohydrate (11.5 g) and 5-iodoanthranilic acid (17.8 g) were dissolved in dimethylformamide (200 mL) and cooled down to 0° C. 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (13.7 g) was added thereto and stirred at room temperature for 16 hours. The organic layer wherein ethyl acetate (1 L) was added was washed with 0.1N sodium hydroxide aqueous solution (200 mL, 100 mL), water (100 mL), 0.1N hydrochloric acid (200 mL) and saturated aqueous solution of sodium chloride (200 mL, 100 mL), respectively. After drying the organic layer over anhydrous sodium sulfate and removing the solvent, a solid material obtained from a mixed solvent of methylene chloride and hexane was filtered to obtain the title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08309561B2
Source datasetuspto-grants-2012_11
ORD IDord-c8bb945771074d1682ed54760e77e603
Source noteuspto-grants-2012_11