Methanol → 1-[(4-Ethoxybenzoyl)amino]cyclopropanecarboxylic acid

HRID 2068525Notes

Reaction equation

HRID 2068525 reaction equation
[CH2:1]([O:3][C:4]1[CH:20]=[CH:19][C:7]([C:8]([NH:10][C:11]2([C:14]([O:16]CC)=[O:15])[CH2:13][CH2:12]2)=[O:9])=[CH:6][CH:5]=1)[CH3:2].O1CCCC1.CO.[OH-].[Li+]>O>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:10][C:11]2([C:14]([OH:16])=[O:15])[CH2:12][CH2:13]2)=[O:9])=[CH:19][CH:20]=1)[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 58304093Ethyl 1-[(4-ethoxybenzoyl)amino]cyclopropanecarboxylate

Product 1

HCID 583041121-[(4-Ethoxybenzoyl)amino]cyclopropanecarboxylic acidYield 99.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

Add ethyl 1-[(4-ethoxybenzoyl)amino]cyclopropanecarboxylate (478 g, 1.72 mol) to tetrahydrofuran (2 L) and methanol (1 L). Dissolve lithium hydroxide (LiOH) (144.7 g, 3.45 mol) in water (1 L) and add it to the mixture. Stir the reaction mixture while heating to 55° C. Cool the reaction to ambient temperature and concentrate under reduced pressure. After removing 2.5 L of solvent, dilute the mixture with water (2 L) and immerse it in an ice water bath. Adjust to pH 2 with aqueous 5N hydrochloric acid (750 mL). Filter the precipitate, wash the cake with water (2×2 L), and dry to give the title compound (425 g, 99%) as a white powder: MS (m/z): 250 (M+1).

Workup

  1. temperatureCool
  2. customthe reaction to ambient temperature
  3. concentrationconcentrate under reduced pressure
  4. customAfter removing 2.5 L of solvent
  5. additiondilute the mixture with water (2 L)
  6. filtrationFilter the precipitate
  7. washwash the cake with water (2×2 L)
  8. customdry

Sources & evidence

ORD record
ord-96efa7d14b8349d7a7def82f7dd0264d
Source dataset
uspto-grants-2012_10
Patent number
US08299061B2

Reaction notes

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