Hydrochloric Acid → 2-((4-Phenylphenyl)formamido)acetic acid

HRID 1351138Notes

Reaction equation

HRID 1351138 reaction equation
C[O:2][C:3](=[O:20])[CH2:4][NH:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)=[O:7].[OH-].[Na+].Cl>>[C:11]1([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:12]=[CH:13][C:8]([C:6]([NH:5][CH2:4][C:3]([OH:20])=[O:2])=[O:7])=[CH:9][CH:10]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 3637091HCID 3637091, compound

Product 1

HCID 2629432-((4-Phenylphenyl)formamido)acetic acidYield 93%

Conditions

Temperature
50 °C

Procedure

[(Biphenyl-4-carbonyl)amino]acetic acid methyl ester (6.58 g, 25 mmol, 1.0 eq., from step (a) above) was added to the flask followed by aqueous sodium hydroxide (1 M, 84 mL, 50 mmol, 2.0 eq). The mixture was heated to 50° C. using an oil bath for 5 hours. The solution was then stirred overnight (16 hours) at room temperature. On cooling, a white precipitate formed. The mixture was cooled further to 5° C. using an ice/water bath. Concentrated hydrochloric acid (8 mL) was added very slowly to the cooled solution, ensuring that the temperature did not rise above 10° C. The mixture was stirred for 15 minutes and was then filtered. The white solid was air dried for 30 minutes and then dried in vacuo at 40° C. for 16 hours to give an off-white solid (5.75 g, 93%).

Workup

  1. customfor 5 hours
  2. temperatureOn cooling
  3. customa white precipitate formed
  4. temperatureThe mixture was cooled further to 5° C.
  5. customdid not rise above 10° C
  6. stirringThe mixture was stirred for 15 minutes
  7. filtrationwas then filtered
  8. customdried for 30 minutes
  9. customdried in vacuo at 40° C. for 16 hours

Sources & evidence

ORD record
ord-995e2a0bd135428599e8c7a53f162a87
Source dataset
uspto-grants-2007_05
Patent number
US07217708B2

Reaction notes

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