Hydrochloric Acid → (S)-3-(3,5-dinitrobenzamido)-3-phenylpropionic acid

HRID 240229Notes

Reaction equation

HRID 240229 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:23]=[C:24]([N+:26]([O-:28])=[O:27])[CH:25]=1)[C:7]([NH:9][C@H:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:11][C:12]([O:14]CC)=[O:13])=[O:8])([O-:3])=[O:2].O.[OH-].[Na+].Cl>O1CCCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:23]=[C:24]([N+:26]([O-:28])=[O:27])[CH:25]=1)[C:7]([NH:9][C@H:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:11][C:12]([OH:14])=[O:13])=[O:8])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 44255974ethyl (S)-3-(3,5-dinitrobenzamido)-3-phenylpropionate

Product 1

HCID 44255973(S)-3-(3,5-dinitrobenzamido)-3-phenylpropionic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

15.4 g of ethyl (S)-3-(3,5-dinitrobenzamido)-3-phenylpropionate from reaction a were dissolved in 100 ml of tetrahydrofuran, and the resulting solution was admixed with 50 ml of water. With vigorous stirring, the slightly cloudy reaction mixture was heated to 45° C., and the pH was adjusted to 13-13.5 with 32% aqueous sodium hydroxide solution and kept constant for the course of the reaction. After the reaction ended (HPLC monitoring >99 area % conversion), the pH of the solution was adjusted to 7-8 by adding 6 N hydrochloric acid, then the organic solvent was distilled off under reduced pressure. The aqueous solution was diluted to 350 ml with water, and the pH was adjusted to 1-2 with 6 N hydrochloric acid with vigorous stirring. The precipitated product was filtered off with suction and washed twice with water. After drying at 40° C. under reduced pressure, a yield of 13.67 g was determined. The HPLC purity was 99.8 area %.

Workup

  1. customWith vigorous stirring, the slightly cloudy reaction mixture
  2. customkept constant for the course of the reaction
  3. distillationthe organic solvent was distilled off under reduced pressure
  4. additionThe aqueous solution was diluted to 350 ml with water
  5. filtrationThe precipitated product was filtered off with suction
  6. washwashed twice with water
  7. customAfter drying at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-e29fc54b805043ecb1f447ef834cec23
Source dataset
uspto-grants-2014_02
Patent number
US08647882B2

Reaction notes

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