Hydrochloric Acid → (2S,4S)-1-allyloxycarbonyl-2-(dimethylcarbamoyl)-4-mercaptopyrrolidine

HRID 1109810Notes

Reaction equation

HRID 1109810 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:12][C@@H:11]2[CH2:13][C@H:8]1[C:9](=[O:14])[S:10]2)=[O:6])[CH:2]=[CH2:3].Cl.[CH3:16][NH:17][CH3:18].C(N(C(C)C)CC)(C)C.Cl>C(#N)C.C(OCC)(=O)C>[CH3:16][N:17]([CH3:18])[C:9]([C@@H:8]1[CH2:13][C@H:11]([SH:10])[CH2:12][N:7]1[C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])=[O:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 15227998(1S,4S)-5-allyloxycarbonyl-2-thia-5-azabicyclo[2.2.1]heptan-3-one

Product 1

HCID 10083864(2S,4S)-1-allyloxycarbonyl-2-(dimethylcarbamoyl)-4-mercaptopyrrolidine

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1S,4S)-5-allyloxycarbonyl-2 -thia-5-azabicyclo[2.2.1]heptan-3-one (39.2 mg) in acetonitrile (1 ml) were added dimethylamine hydrochloride (16.5 mg) and diisopropylethylamine (35.7 mg). The mixture was stirred for 3 hours at room temperature. After the reaction was over, 1N-hydrochloric acid (0.092 ml) was added thereto, and the mixture was diluted with ethyl acetate (2 ml) and dried over magnesium sulfate. Distillation of the solent, followed by purifying the residue by silica gel chromatography, gave oily (2S,4S) -N,N-dimethyl-1-allyloxycarbonyl-4-mercapto-2-pyrrolidinecarboxamide.

Workup

  1. additionwas added
  2. dry with materialdried over magnesium sulfate
  3. distillationDistillation of the solent,
  4. customby purifying the residue by silica gel chromatography

Sources & evidence

ORD record
ord-40a5c98f6bf641079163be8d215c36e7
Source dataset
uspto-grants-1994_06
Patent number
US05322952

Reaction notes

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