1,2-Dichloroethane → HCID 53738574, compound

HRID 1588851Notes

Reaction equation

HRID 1588851 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:19])[NH:10][CH:11]([CH2:15]CSC)[C:12](O)=O)[CH:5]=[CH:6][CH:7]=1.[NH:20]([CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[S:35](Cl)(Cl)=O.C(=O)(O)[O-].[Na+].Cl[CH2:45][CH2:46]Cl>>[CH3:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:19])[NH:10][CH:11]([CH2:12][CH2:45][CH3:46])[C:15]([N:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[S:35])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 3984575HCID 3984575, compoundHCID 12433731HCID 12433731, compound

Product 1

HCID 53738574HCID 53738574, compound

Procedure

A suspension of (RS)-2-[3-(3-methylphenyl)ureido]-4-(methylthio)butanoic acid (4.5 g) and tert-butyl anilinoacetate (3.3 g) in anhydrous 1,2-dichloroethane (300 cc) is heated to reflux until a solution is obtained. Thionyl chloride (1.16 cc) is then added, refluxing being maintained until the gaseous evolution has ceased. The reaction mixture is then poured into a saturated aqueous sodium bicarbonate solution (100 cc) and the organic phase is washed with water (100 cc), dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. The oily residue obtained is purified by chromatography on silica gel (0.04-0.063 mm; 350 g) contained in a column 5 cm in diameter [eluant: methylene chloride/methanol (98:2 by volume)], using an excess pressure of 40 kPa of nitrogen and collecting 100-cc fractions. Fractions 12 to 28 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. By recrystallization of the residue thereby obtained in diethyl ether, tert-butyl (RS)-N-{2-[3-(3-methylphenyl)ureido]-4-methylthiobutyryl}-N-phenylglycinate (2.8 g), m.p. 142° C., is obtained.

Workup

  1. temperatureis heated
  2. temperatureto reflux until a solution
  3. customis obtained
  4. temperaturerefluxing
  5. temperaturebeing maintained until the gaseous evolution
  6. washthe organic phase is washed with water (100 cc)
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  9. customThe oily residue obtained
  10. customis purified by chromatography on silica gel (0.04-0.063 mm; 350 g)
  11. customcollecting 100-cc fractions
  12. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  13. customBy recrystallization of the residue
  14. customthereby obtained in diethyl ether

Sources & evidence

ORD record
ord-22797059c5854cc2bf8de5539ee8b610
Source dataset
uspto-grants-1993_06
Patent number
US05223529

Reaction notes

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