Hydrochloric Acid → HCID 66653440, compound

HRID 1524276Notes

Reaction equation

HRID 1524276 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:26])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C@@H:13]([C:15](=[O:25])[NH:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][CH:18]=2)[CH3:14])[CH:7]=1.O.Cl>CO>[C:23]([C:20]1[CH:19]=[CH:18][C:17]([NH:16][C:15]([C@H:13]([O:12][C:8]2[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=2)[C:5]([OH:26])=[O:4])[CH3:14])=[O:25])=[CH:22][CH:21]=1)#[N:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 8532025HCID 8532025, compound

Product 1

HCID 66653440HCID 66653440, compoundYield 218.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Add 10% aqueous solution of sodium hydroxide (2.5 mL, 6.2 mmol) to a suspension of 3-[(R)-1-(4-cyano-phenylcarbamoyl)-ethoxy]-benzoic acid methyl ester (0.59 g, 0.81 mmol) in a 1:1 mixture of water: MeOH (20 mL). Heat the mixture at 50° C. for 1 h then cool to room temperature and adjust the pH of the mixture to approximately pH 5 by the addition of a 2 N solution of hydrochloric acid. Extract the mixture with EtOAc and wash the combined organic phase with brine, dry over anhydrous sodium sulfate and concentrate under reduced pressure to provide 0.55 g of 3-[(R)-1-(4-cyano-phenylcarbamoyl)-ethoxy]-benzoic acid as a foam.

Workup

  1. temperaturethen cool to room temperature
  2. extractionExtract the mixture with EtOAc
  3. washwash the combined organic phase with brine
  4. dry with materialdry over anhydrous sodium sulfate
  5. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-962134ef99e6428ea3da5e56b0d58fc6
Source dataset
uspto-grants-2015_07
Patent number
US09079880B2

Reaction notes

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