Dimethyl Sulfoxide → HCID 15117313, compound

HRID 1029670Notes

Reaction equation

HRID 1029670 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([O:14][C:15]([N:17]1[CH2:21][CH:20]([CH:22]([OH:24])[CH3:23])[CH2:19][N:18]1[C:25](=[O:29])[N:26]([CH3:28])[CH3:27])=[O:16])[CH:12]=[CH2:13].C(N(CC)CC)C>ClCCl>[C:22]([CH:20]1[CH2:19][N:18]([C:25](=[O:29])[N:26]([CH3:27])[CH3:28])[N:17]([C:15]([O:14][CH2:11][CH:12]=[CH2:13])=[O:16])[CH2:21]1)(=[O:24])[CH3:23]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 15117312HCID 15117312, compound

Product 1

HCID 15117313HCID 15117313, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of oxalyl chloride (7.42 ml) in dichloromethane (250 ml) was added dropwise dimethyl sulfoxide (12.7 ml) at -70° C. To this reaction mixture was added dropwise a solution of 2-allyloxycarbonyl-1-dimethylcarbamoyl-4-(1-hydroxyethyl)pyrazolidine (22 g) in dichloromethane (40 ml), and then was added dropwise triethylamine (56.5 ml) at -70° C. The reaction mixture was allowed to warm to room temperature. The precipitate was filtered off and the filtrate was concentrated in vacuo. The residue was poured into a mixture of ethyl acetate and 1N-aqueous hydrochloric acid, and the organic layer was extracted, washed with brine, and dried over magnesium sulfate. Evaporation of the solvent gave a residual oil, which was chromatographed on silica gel eluting in turn with a mixture of hexane and ethyl acetate (1:2, V/V) and ethyl acetate to give 4-acetyl-2-allyloxycarbonyl-1-dimethylcarbamoylpyrazolidine (21.3 g).

Workup

  1. filtrationThe precipitate was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionThe residue was poured into a mixture of ethyl acetate and 1N-aqueous hydrochloric acid
  4. extractionthe organic layer was extracted
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. customEvaporation of the solvent
  8. customgave a residual oil, which
  9. customwas chromatographed on silica gel eluting in turn with a mixture of hexane and ethyl acetate (1:2, V/V) and ethyl acetate

Sources & evidence

ORD record
ord-1c4dc93ef56d4d91b4a9024e254cc305
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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