Methanol → 3-[(4-Cyano-phenylcarbamoyl)-methoxy]-benzoic acid

HRID 1524267Notes

Reaction equation

HRID 1524267 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:25])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][C:14](=[O:24])[NH:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][CH:17]=2)[CH:7]=1.CO.O1CCCC1>O>[C:22]([C:19]1[CH:18]=[CH:17][C:16]([NH:15][C:14]([CH2:13][O:12][C:8]2[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=2)[C:5]([OH:25])=[O:4])=[O:24])=[CH:21][CH:20]=1)#[N:23]

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 81734983-[(4-Cyano-phenylcarbamoyl)-methoxy]-benzoic acid methyl ester

Product 1

HCID 454173003-[(4-Cyano-phenylcarbamoyl)-methoxy]-benzoic acidYield 60.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Add lithium hydroxide (0.10 g, 4.18 mmol) to a suspension of 3-[(4-cyano-phenylcarbamoyl)-methoxy]-benzoic acid methyl ester (0.50 g, 1.61 mmol) in a 1:1:1 mixture of water: MeOH: tetrahydrofuran. Stir the mixture at room temperature for 36 h then dilute with water and wash with EtOAc. Adjust the pH of the aqueous phase by the addition of a 1 N solution of hydrochloric acid. Extract the mixture with EtOAc and dry the combined organic phase over anhydrous sodium sulfate. Concentrate under reduced pressure to provide 0.290 g of 3-[(4-cyano-phenylcarbamoyl)-methoxy]-benzoic acid as a solid.

Workup

  1. washwash with EtOAc
  2. additionby the addition of a 1 N solution of hydrochloric acid
  3. extractionExtract the mixture with EtOAc
  4. dry with materialdry the combined organic phase over anhydrous sodium sulfate
  5. concentrationConcentrate under reduced pressure

Sources & evidence

ORD record
ord-23d532fadd6b4f57b0e36ea9c1395946
Source dataset
uspto-grants-2015_07
Patent number
US09079880B2

Reaction notes

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