Hydrochloric Acid → HCID 66653302, compound

HRID 1524280Notes

Reaction equation

HRID 1524280 reaction equation
C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C@H:11]([C:13](=[O:23])[NH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=2)[CH3:12])[CH:5]=1.CO.[OH-].[Na+].Cl>O>[C:21]([C:18]1[CH:17]=[CH:16][C:15]([NH:14][C:13]([C@@H:11]([O:10][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([OH:24])=[O:2])[CH3:12])=[O:23])=[CH:20][CH:19]=1)#[N:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 8532015HCID 8532015, compound

Product 1

HCID 66653302HCID 66653302, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

Heat a suspension of 3-[(S)-1-(4-cyano-phenylcarbamoyl)-ethoxy]-benzoic acid methyl ester (0.42 g, 1.30 mmol) in a 1:1 mixture of MeOH:water (10 mL) to 50° C. and add sodium hydroxide (1.0 mL, 2.5 mmol) as a 10% aqueous solution. Stir the mixture at 50° C. for 1 h during which time all of the solids dissolve. Cool the reaction mixture 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. Dilute the mixture with water and extract with methylene chloride. Dry the combined organic phase over anhydrous sodium sulfate and concentrate under reduced pressure to provide 0.38 g of 3-[(S)-1-(4-cyano-phenylcarbamoyl)-ethoxy]-benzoic acid as a foam.

Workup

  1. temperatureHeat
  2. dissolutiondissolve
  3. temperatureCool the reaction mixture to room temperature
  4. extractionextract with methylene chloride
  5. dry with materialDry the combined organic phase over anhydrous sodium sulfate
  6. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-785086f536434237ba9bc0344ee707ef
Source dataset
uspto-grants-2015_07
Patent number
US09079880B2

Reaction notes

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