Citric Acid → HCID 54225044, compound

HRID 850486Notes

Reaction equation

HRID 850486 reaction equation
[NH2:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:4]2[C:5]([N:7]([CH2:10][CH2:11][C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)[C:8](=[O:9])[C:3]=12)=[O:6].Cl[C:23](=[O:28])[CH2:24][CH2:25][CH2:26][CH3:27].C(N(CC)CC)C.[C:36](O)(=O)[CH2:37][C:38]([CH2:43][C:44](O)=[O:45])(C(O)=O)O>CC(C)=O>[C:23]([O:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][CH2:10][N:7]2[C:8](=[O:9])[C:3]3[C:4](=[CH:19][CH:20]=[CH:21][C:2]=3[NH:1][C:44](=[O:45])[CH2:43][CH2:38][CH2:37][CH3:36])[C:5]2=[O:6])=[CH:13][CH:14]=1)(=[O:28])[CH2:24][CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8471TriethylamineHCID 61186Valeryl chlorideHCID 19363369HCID 19363369, compound

Product 1

HCID 54225044HCID 54225044, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-Amino-N-[2-(4-hydroxyphenyl)ethyl]phthalimide (110 mg, 0.390 mol, 1 eq) was dissolved in acetone (30 ml), and to this solution were added 1-chloro-1-pentanone (70.5 mg, 0.585 mmol, 1.5 eq) and triethylamine (0.081 ml, 0.585 mol, 1.5 eq) in this order. The mire was refluxed under heating for 30 minutes. This reaction mixture was cooled to room temperature. Ice water (10 ml) and citric acid (10 ml) were added, and the mixture was extracted twice with ethyl acetate (20 ml). The organic layers were combined, washed with saturated brine (30 ml) and dried over anhydrous sodium sulfate. After the drying agent was filtered off, the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=5/1) to give 4-[2-(1,3-dioxo4-pentanoylamino-1,3-dihydroisoindol-2-yl)ethyl]phenyl pentanoate (80.2 mg, 56.2%) as colorless crystals.

Workup

  1. temperatureThe mire was refluxed
  2. temperatureunder heating for 30 minutes
  3. extractionthe mixture was extracted twice with ethyl acetate (20 ml)
  4. washwashed with saturated brine (30 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter the drying agent was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe obtained residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-cb012d53d1704814ad0241af02c31b93
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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