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

HRID 1875563Notes

Reaction equation

HRID 1875563 reaction equation
[CH:1]([O:4][C:5](=[O:26])[C@H:6]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=1)[NH:7][C:8](=[O:17])[C:9]1[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:16])([CH3:3])[CH3:2].O.ON1C2C=CC=CC=2N=N1.[I:38][C:39]1[CH:47]=[C:43]([C:44](O)=[O:45])[C:42]([NH2:48])=[CH:41][CH:40]=1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(OCC)(=O)C>[CH:1]([O:4][C:5](=[O:26])[C@H:6]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([NH:25][C:44](=[O:45])[C:43]2[CH:47]=[C:39]([I:38])[CH:40]=[CH:41][C:42]=2[NH2:48])=[CH:23][CH:24]=1)[NH:7][C:8](=[O:17])[C:9]1[C:10]([Cl:16])=[CH:11][CH:12]=[CH:13][C:14]=1[Cl:15])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 72911Benzoic acid, 2-amino-5-iodo-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 580183184-Amino-N-(2,6-dichlorobenzoyl)-L-phenylalanine Isopropylester

Product 1

HCID 866008854-[(2-amino-5-iodobenzoyl)amino]-N-(2,6-dichlorobenzoyl)-L-phenylalanine isopropylester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  1. washwas 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)
  2. dry with materialAfter drying the organic layer over anhydrous sodium sulfate
  3. customremoving the solvent
  4. customa solid material obtained from a mixed solvent of methylene chloride and hexane
  5. filtrationwas filtered

Sources & evidence

ORD record
ord-c8bb945771074d1682ed54760e77e603
Source dataset
uspto-grants-2012_11
Patent number
US08309561B2

Reaction notes

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