Hydrochloric Acid → HCID 56982543, compound

HRID 1650272Notes

Reaction equation

HRID 1650272 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH2:5]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([OH:16])[CH2:13][C@H:12]1[CH:17]=[C:18]([CH3:22])[C:19](=[O:21])[CH3:20])=[O:10])[CH:6]=[CH2:7].[CH3:23][NH:24][CH3:25].Cl>C1(C)C=CC=CC=1.O1CCCC1.O.C(OCC)(=O)C.C(N(CC)CC)C>[CH2:5]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][C:1](=[O:2])[N:24]([CH3:25])[CH3:23])[CH2:13][C@H:12]1[CH:17]=[C:18]([CH3:22])[C:19](=[O:21])[CH3:20])=[O:10])[CH:6]=[CH2:7]

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 6371PhosgeneHCID 57026776HCID 57026776, compound

Product 1

HCID 56982543HCID 56982543, compound

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of phosgene (2.5 ml) in toluene (15 ml) were added in turn triethylamine (1.45 ml) and a solution of (2S,4R)-1-allyloxycarbonyl-4-hydroxy-2-(2-methyl-3-oxo-1-butenyl)pyrrolidine (2.50 g) in toluene (10 ml) at 0° C. After stirring at 0° C. for 2 hours, the mixture was evaporated in vacuo and the residue was taken up into toluene (15 ml). Evaporation of the solvent gave a residue, which was dissolved in tetrahydrofuran (5 ml). This solution was added dropwise to a solution of dimethylamine (0.89 g) in a mixture of water (50 ml) and tetrahydrofuran (50 ml) under stirring at 0° C., and the stirring was continued for additional 10 minutes at 0° C. After adjusting pH to 7 with 1N hydrochloric acid, the mixture was diluted with ethyl acetate (200 ml). The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (100 ml) eluting with a mixture of n-hexane and ethyl acetate (6:4 V/V) to give (2S,4R)-1-allyloxycarbonyl-4-(dimethylcarbamoyloxy)-2- -(2-methyl-3-oxo-1-butenyl)pyrrolidine (2.65 g). IR (Neat): 1700, 1665 cm-1

Workup

  1. customat 0° C
  2. customthe mixture was evaporated in vacuo
  3. customEvaporation of the solvent
  4. customgave a residue, which
  5. stirringunder stirring at 0° C.
  6. waitthe stirring was continued for additional 10 minutes at 0° C
  7. customThe organic layer was separated
  8. washwashed with brine
  9. dry with materialdried over magnesium sulfate
  10. customevaporated
  11. customThe residue was chromatographed on silica gel (100 ml)
  12. washeluting with a mixture of n-hexane and ethyl acetate (6:4 V/V)

Sources & evidence

ORD record
ord-93495c158ad34ae1bc60fbeba683e91b
Source dataset
uspto-grants-1990_05
Patent number
US04923857

Reaction notes

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