Hydrochloric Acid → (2S,4S)-N-(2-phenylethyl)-1-allyloxycarbonyl-4-mercapto-2-pyrrolidinecarboxamide

HRID 1109812Notes

Reaction equation

HRID 1109812 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].[C:15]1([CH2:21][CH2:22][NH2:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl>O1CCCC1.C(OCC)(=O)C>[C:15]1([CH2:21][CH2:22][NH:23][C:9]([C@@H:8]2[CH2:13][C@H:11]([SH:10])[CH2:12][N:7]2[C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])=[O:14])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 1001PhenethylamineHCID 15227998(1S,4S)-5-allyloxycarbonyl-2-thia-5-azabicyclo[2.2.1]heptan-3-one

Product 1

HCID 57144107(2S,4S)-N-(2-phenylethyl)-1-allyloxycarbonyl-4-mercapto-2-pyrrolidinecarboxamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1S,4S)-5-allyloxycarbonyl-2-thia-5-azabicyclo[2.2.1]heptan-3-one (32.2 mg) in tetrahydrofuran (1 ml) was added 2-phenylethylamine (20.1 mg). The mixture was stirred for 4 hours at room temperature. After the reaction was over, 1N-hydrochloric acid (0.027 ml) was added thereto, and the mixture was diluted with ethyl acetate (2 ml) and dried over magnesium sulfate. Distillation of the solvent, followed by purifying the residue by silica gel chromatography, gave oily (2S,4S) -N-(2-phenylethyl)-1-allyloxycarbonyl-4-mercapto-2-pyrrolidinecarboxamide.

Workup

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

Sources & evidence

ORD record
ord-969520bccd934c569ba9e585db349b2e
Source dataset
uspto-grants-1994_06
Patent number
US05322952

Reaction notes

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