Acetic Acid → HCID 18602497, compound

HRID 1381163Notes

Reaction equation

HRID 1381163 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]([O:17]CC#N)=O)=[CH:10][C:9]=2[CH3:21])=[O:7])=[CH:4][CH:3]=1.Cl.[CH3:25][O:26][C:27](=[O:31])[C@H:28]([CH3:30])[NH2:29].C(O)(=O)C.C(N(CC)CC)C>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]([NH:29][C@H:28]([C:27]([O:26][CH3:25])=[O:31])[CH3:30])=[O:17])=[CH:10][C:9]=2[CH3:21])=[O:7])=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8471Triethylamine3×HCID 2733257Alanine methyl ester hydrochloride2×HCID 13277466HCID 13277466, compound

Product 1

HCID 18602497HCID 18602497, compoundYield 169.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 10.0 g (0.03 mole) of cyanomethyl [5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-yl]acetate, 1.6 g (0.015 mole) of alanine methyl ester hydrochloride, 0.3 ml of glacial acetic acid, and 2.1 ml (0.015 mole) triethylamine in 40 ml of THF was heated under reflux for 31/2 hours. A second addition of 1.6 g of alanine methyl ester hydrochloride and 2.1 ml of triethylamine was made. The mixture was heated under reflux for 2 hours. A fourth addition of 2.0 g (0.018 mole) of triethylamine was made. The mixture was heated under reflux for 16 hours. The reaction was partitioned between chloroform and dilute hydrochloric acid. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo. The residue was recrystallized from acetonitrile to give 9.6 g of methyl N-{[5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-yl]acetyl}alaninate, m.p. 163°-165° C. (85% yield).

Workup

  1. temperatureunder reflux for 31/2 hours
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 2 hours
  4. temperatureThe mixture was heated
  5. temperatureunder reflux for 16 hours
  6. customThe reaction was partitioned between chloroform and dilute hydrochloric acid
  7. washThe organic layer was washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated in vacuo
  10. customThe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-808b895702b34b428b85ee252a517d1c
Source dataset
uspto-grants-1986_04
Patent number
US04585784

Reaction notes

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