Citric Acid → HCID 19735035, compound

HRID 326720Notes

Reaction equation

HRID 326720 reaction equation
[C:1]([CH:3]([CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)[C:4]([OH:6])=[O:5])#[N:2].[Cl:17][C:18]1[CH:23]=[C:22]([Cl:24])[C:21]([Cl:25])=[CH:20][C:19]=1[OH:26].CCN=C=NCCCN(C)C.Cl.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl>[C:1]([CH:3]([CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)[C:4]([O:6][CH2:18][CH3:19])=[O:5])#[N:2].[Cl:17][C:18]1[CH:23]=[C:22]([Cl:24])[C:21]([Cl:25])=[CH:20][C:19]=1[O:26][C:4](=[O:5])[CH:3]([C:1]#[N:2])[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 72712,4,5-TrichlorophenolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19735046HCID 19735046, compound

Product 2

HCID 19735035HCID 19735035, compoundHCID 53675740HCID 53675740, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Cyano-3-(3-indolyl)propionic acid from Step a, 2,4,5-trichlorophenol (394 mg, 2 mmol) and EDCl (392 mg, 2 mmol) were combined in methylene chloride (10 mL) and the reaction mixture was stirred at ambient temperature overnight. The reaction mixture was added to 20 mL of 10% citric acid solution and the aqueous mixture was extracted with methylene chloride. The methylene chloride was evaporated under reduced pressure and the residue was purified by flash chromatography on silica gel eluting with ethyl acetate/hexane (1:4 to 1:2) to give 210 mg (37% yield from ethyl 2-cyano-3-(3-indolyl)propionate) of the title compound.

Workup

  1. extractionthe aqueous mixture was extracted with methylene chloride
  2. customThe methylene chloride was evaporated under reduced pressure
  3. customthe residue was purified by flash chromatography on silica gel eluting with ethyl acetate/hexane (1:4 to 1:2)

Sources & evidence

ORD record
ord-463fe5aa312b4a6d9030c9e0a7bb87e9
Source dataset
uspto-grants-1993_12
Patent number
US05270302

Reaction notes

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