Dimethylformamide → HCID 19600857, compound

HRID 609889Notes

Reaction equation

HRID 609889 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:16]2[N:20]([CH2:21][CH2:22][CH2:23]O)[C:19](=[O:25])[CH:18]([CH2:26][C:27](O)=[O:28])[S:17]2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:32])=O.CN(C)C=O.[NH:39]1[CH2:43][CH2:42][CH2:41][CH2:40]1>ClCCl>[C:12]([C:9]1[CH:8]=[C:7]([CH:16]2[N:20]([CH2:21][CH2:22][CH2:23][Cl:32])[C:19](=[O:25])[CH:18]([CH2:26][C:27]([N:39]3[CH2:43][CH2:42][CH2:41][CH2:40]3)=[O:28])[S:17]2)[CH:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:10]=1[OH:11])([CH3:14])([CH3:15])[CH3:13]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 31268PyrrolidineHCID 19600888HCID 19600888, compound

Product 1

HCID 19600857HCID 19600857, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 2-(3,5-di-tert-butyl-4-hydroxyphenyl)-3-(3-hydroxypropyl)-5-carboxymethyl-1,3-thiazolidin-4-one (0.61 g) obtained in Reference Example 41 in dichloromethane (20 ml) were added thionyl chloride (0.38 g) and a catalytic amount of dimethylformamide, and the mixture was refluxed for 2 hours. After allowing to cool, the mixture was added dropwise to a solution of pyrrolidine (1.02 g) in dichloromethane (20 ml) under cooling with ice, and stirred at that temperature for 1 hour. After completion of the reaction, the reaction mixture was poured into ice-water and extracted with chloroform. The organic layer was washed successively with 1N hydrochloric acid and brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; chloroform-methanol, 97:3) and then recrystallized from chloroform/n-hexane to yield 0.65 g (92%) of the title compound as colorless crystals. mp 193-194° C. NMR (CDCl3) (200 MHz) δ: 1.43 (18H, s), 1.4-2.2 (6H, m), 2.5-3.1 (2H, m), 3.2-3.7 (8H, m), 4.2-4.5 (1H, m), 5.29 (1H, s), 5.53 (1H, s), 7.08 (2H, s)

Workup

  1. temperatureto cool
  2. temperatureunder cooling with ice
  3. customAfter completion of the reaction
  4. extractionextracted with chloroform
  5. washThe organic layer was washed successively with 1N hydrochloric acid and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (eluent; chloroform-methanol, 97:3)
  9. customrecrystallized from chloroform/n-hexane

Sources & evidence

ORD record
ord-00382a5b6dfc478f84d221e95883c259
Source dataset
uspto-grants-1999_12
Patent number
US05998452

Reaction notes

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