Hydrogen chloride-ethyl acetate → HCID 22467404, compound

HRID 1934717Notes

Reaction equation

HRID 1934717 reaction equation
C(OC([NH:8][C:9]1[CH:33]=[CH:32][C:12]([CH2:13][NH:14][C:15](=[O:31])[C:16]2[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=2[NH:25][CH:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)=[C:11]([Cl:34])[CH:10]=1)=O)(C)(C)C.C(OC(=O)C)C.Cl>C(OCC)(=O)C>[NH2:8][C:9]1[CH:33]=[CH:32][C:12]([CH2:13][NH:14][C:15](=[O:31])[C:16]2[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=2[NH:25][CH:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)=[C:11]([Cl:34])[CH:10]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 22467491HCID 22467491, compound

Product 1

HCID 22467404HCID 22467404, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-[4-(tert-butoxycarbonyl)amino-2-chlorobenzyl]-2-(cyclopentylamino)-5-nitrobenzamide (141 mg) in anhydrous ethyl acetate (2 mL) was added 4N-hydrochloric acid ethyl acetate solution. (4 mL). After stirring for 2 hours at ambient temperature, the mixture was partitioned between 1N-sodium hydroxide solution and chloroform. The separated organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with diisopropyl ether to give N-(4-amino-2-chlorobenzyl)-2-(cyclopentylamino)-5-nitrobenzamide as yellow powders (102 mg).

Workup

  1. customthe mixture was partitioned between 1N-sodium hydroxide solution and chloroform
  2. washThe separated organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-d5c1ae7143f648d6b6fbe740e0e0f8cd
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

Loading…