Thionyl Chloride → HCID 15660876, compound

HRID 344697Notes

Reaction equation

HRID 344697 reaction equation
ClC(O[CH2:5][CH:6](C)C)=O.[CH3:9][N:10]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:11]([CH2:13][CH2:14][C:15]([OH:17])=O)=[O:12].[NH:25]1[CH2:29][CH2:28][CH2:27][C@H:26]1[CH:30]([OH:34])[C:31]([OH:33])=[O:32].S(Cl)(Cl)=O>C1COCC1.C(O)C.C(N(CC)CC)C>[CH2:5]([O:32][C:31](=[O:33])[CH:30]([C@@H:26]1[CH2:27][CH2:28][CH2:29][N:25]1[C:15](=[O:17])[CH2:14][CH2:13][C:11](=[O:12])[N:10]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:9])[OH:34])[CH3:6]

Participants

8

Reactant 4

HCID 24386Thionyl ChlorideHCID 62365Isobutyl chloroformateHCID 845833HCID 845833, compoundHCID 10844510HCID 10844510, compound

Product 1

HCID 15660876HCID 15660876, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent2×

Conditions

Temperature
-15 °C

Procedure

Triethylamine (3.5 ml) and isobutyl chloroformate (980 μl) were added to a solution of 3-(N-methyl-N-benzylcarbamoyl) propionic acid (1.33 g) in THF (16 ml). The mixture was stirred for 15 mins at -15° C. The solution was named solution A. (2RS)-2-[(2S)-pyrrolidin-2-yl]-2-hydroxyacetic acid (1.0 g) was dissolved in ethanol (25 ml). The solution was cooled to -20° C. Thionyl chloride (1.0 ml) was added dropwise to the cooled solution. The mixture was stirred for 2 hrs. at room temperature. Triethylamine (5 ml) was added dropwise to the solution cooled to -20° C. again. The solution was allowed to stand to rise to room temperature, and evaporated. THF (26 ml) and triethylamine (1.15 ml) were added to the residue. To the solution cooled to -10° C, the above solution A was added dropwise. The mixture was stirred for 2 hrs at room temperature. Water was added to the reaction solution. The mixture was extracted with EtOAc. The extract was washed, dried and evaporated. The residue was purified by column chromatography on silica gel (hexane-EtOAc) to give the title compound (1.67 g) having the following physical data:

Workup

  1. temperatureThe solution was cooled to -20° C
  2. stirringThe mixture was stirred for 2 hrs
  3. customat room temperature
  4. temperaturecooled to -20° C. again
  5. customto rise to room temperature
  6. customevaporated
  7. additionTHF (26 ml) and triethylamine (1.15 ml) were added to the residue
  8. temperatureTo the solution cooled to -10° C
  9. additionthe above solution A was added dropwise
  10. stirringThe mixture was stirred for 2 hrs at room temperature
  11. additionWater was added to the reaction solution
  12. extractionThe mixture was extracted with EtOAc
  13. washThe extract was washed
  14. customdried
  15. customevaporated
  16. customThe residue was purified by column chromatography on silica gel (hexane-EtOAc)

Sources & evidence

ORD record
ord-ccb4157f229245a1989eb6f6a7133c64
Source dataset
uspto-grants-1991_10
Patent number
US05053414

Reaction notes

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