Sodium Hydroxide → 2-(4-Methoxy-benzoylamino)-pent-4-enoic acid

HRID 479140Notes

Reaction equation

HRID 479140 reaction equation
C([O:3][C:4](=[O:20])[CH:5]([NH:9][C:10](=[O:19])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)[CH2:6][CH:7]=[CH2:8])C.[OH-].[Na+]>C1COCC1.CCO>[CH3:18][O:17][C:14]1[CH:13]=[CH:12][C:11]([C:10]([NH:9][CH:5]([CH2:6][CH:7]=[CH2:8])[C:4]([OH:20])=[O:3])=[O:19])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 695565842-(4-Methoxy-benzoylamino)-pent-4-enoic acid ethyl ester

Product 1

HCID 180035572-(4-Methoxy-benzoylamino)-pent-4-enoic acid

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

10.56 g of the above prepared 2-(4-methoxy-benzoylamino)-pent-4-enoic acid ethyl ester (38.1 mmol) was dissolved in 120 ml of THF/EtOH=1/1 and treated at 0° with 38 ml of 2N NaOH. The reaction mixture was kept at this temperature for 3 h. It was then poured onto crashed ice/HCl, extracted twice with AcOEt, washed with brine, and dried over natrium sulfate. Evaporation of the solvents, followed by crystallisation from AcOEt at −20°, yielded 8.41 g of the title acid as white crystals of m.p. 121-124°.

Workup

  1. additionIt was then poured
  2. extractionextracted twice with AcOEt
  3. washwashed with brine
  4. dry with materialdried over natrium sulfate
  5. customEvaporation of the solvents
  6. customfollowed by crystallisation from AcOEt at −20°
  7. customyielded 8.41 g of the title acid as white crystals of m.p. 121-124°

Sources & evidence

ORD record
ord-c1378c4b521643cfbd65089ab9f25ad2
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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