Hydrochloric Acid → N-(2,6-Dichlorobenzoyl)-4-nitro-L-phenylalanine

HRID 557444

Reaction equation

HRID 557444 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([CH2:8][C@@H:9]([C:11]([OH:13])=[O:12])[NH2:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[Na+].[Cl:18][C:19]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:20]=1[C:21](Cl)=[O:22].Cl>O.CC(C)=O>[Cl:18][C:19]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:20]=1[C:21]([NH:10][C@H:9]([C:11]([OH:13])=[O:12])[CH2:8][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:15][CH:14]=1)=[O:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 137064-Nitro-3-phenyl-L-alanineHCID 14798Sodium HydroxideHCID 783922,6-Dichlorobenzoyl chloride

Product 1

HCID 58018322N-(2,6-Dichlorobenzoyl)-4-nitro-L-phenylalanineYield 95%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To 13 mL of acetone, there were added 10.04 g of p-nitro-L-phenylalanine and 28 mL of water to thus form a suspension and the latter was cooled in an ice-bath. To this suspension, there were alternatively dropwise added 18.4 mL of a 6M sodium hydroxide solution and 10.05 g of 2,6-dichlorobenzoyl chloride in such a manner that the pH value of the suspension was maintained at a level of not less than 13 at a temperature of not more than 15° C. After the completion of the dropwise addition, the suspension was further stirred for 2 hours with cooling in an ice-bath, then the progress of the reaction was confirmed by HPLC and 36 mL of a 2M hydrochloric acid solution was dropwise added while taking care to prevent any excess generation of heat. The suspension containing separated solid matter was stirred at 10° C. overnight, the precipitates were isolated through filtration and then dried under reduced pressure at 60° C. to thus obtain 17.32 g of the title compound as a white crystalline solid (yield: 95%).

Workup

  1. customto thus form a suspension
  2. temperaturethe latter was cooled in an ice-bath
  3. temperaturewas maintained at a level of not less than 13 at a temperature of not more than 15° C
  4. additionAfter the completion of the dropwise addition
  5. temperaturewith cooling in an ice-bath
  6. additionwas dropwise added
  7. temperatureof heat
  8. additionThe suspension containing
  9. customseparated solid matter
  10. stirringwas stirred at 10° C. overnight
  11. customthe precipitates were isolated through filtration

Sources & evidence

ORD record
ord-f9bc27c3ea1f4d2a945f7ebc40118fe7
Source dataset
uspto-grants-2011_11
Patent number
US08058432B2

Linked notes

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