Water → HCID 22815445, compound

HRID 443744Notes

Reaction equation

HRID 443744 reaction equation
[CH3:1][C:2](=[CH2:13])[C:3]([N:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[C:10]([OH:12])=[O:11])=[O:4].[O:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[C:19](=[S:21])[OH:20].C(Cl)Cl.O>C(O)C>[O:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[C:19]([S:21][CH2:13][CH:2]([CH3:1])[C:3]([N:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[C:10]([OH:12])=[O:11])=[O:4])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 132083491-(2-Methylacryloyl)-L-prolineHCID 178526141HCID 178526141, compound

Product 1

HCID 22815445HCID 22815445, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

11.4 g (2S)-1-(2- methyl-2-propenoyl)-2-pyrrolidine carboxylic acid are dissolved in 16.5 ml ethanol and 10 g furan-2-thiocarboxylic acid are added dropwise over 15 minutes. The reaction mixture is stirred overnight at room temperature, and methylene chloride and water (9:1) are then added. The so obtained organic phase is decanted and extracted with 0.5 N NaOH. The combined aqueous phases are adjusted to pH 4 and then twice extracted with 0.5 l CH2Cl2. The combined organic phases are dried over MgSO4, filtered and the solvent is evaporated. The residue is dissolved in CH2Cl2 /ether (1:4) and 6 ml tert-butylamine dissolved in ether are added; the tert-butyl ammonium salt of the title compound precipitates (M.P. 132°-140°) ([α]D20 =-67.3°; c=2.2 in H2O).

Workup

  1. customThe so obtained organic phase
  2. customis decanted
  3. extractionextracted with 0.5 N NaOH
  4. extractiontwice extracted with 0.5 l CH2Cl2
  5. dry with materialThe combined organic phases are dried over MgSO4
  6. filtrationfiltered
  7. customthe solvent is evaporated
  8. dissolutionThe residue is dissolved in CH2Cl2 /ether (1:4)
  9. dissolution6 ml tert-butylamine dissolved in ether
  10. additionare added
  11. customthe tert-butyl ammonium salt of the title compound precipitates (M.P. 132°-140°) ([α]D20 =-67.3°; c=2.2 in H2O)

Sources & evidence

ORD record
ord-696c3354889548e7a196af5b0a2782cd
Source dataset
uspto-grants-1981_04
Patent number
US04261895

Reaction notes

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