Iodoethane → HCID 18600216, compound

HRID 1583568Notes

Reaction equation

HRID 1583568 reaction equation
[CH3:1][C@H:2]([N:6]1CCC[C:7]1=[O:11])[C:3]([OH:5])=[O:4].C(I)C.[CH2:15]([S:22]CBr)[C:16]1[CH:21]=[CH:20]C=[CH:18][CH:17]=1>>[CH2:21]([C:16]1([CH2:15][SH:22])[CH2:17][CH2:18][N:6]([C@@H:2]([CH3:1])[C:3]([OH:5])=[O:4])[C:7]1=[O:11])[CH3:20]

Participants

4

Reactant 3

HCID 6340IodoethaneHCID 4067177BenzylthiobromomethaneHCID 7175678(S)-2-(2-oxopyrrolidin-1-yl)propanoic acid

Product 1

HCID 18600216HCID 18600216, compound

Procedure

Following the procedures of Examples 1C-1E, α(S)-methyl-2-oxo-1-pyrrolidineacetic acid was first alkylated with ethyl iodide and then with benzylmercaptomethyl bromide. Removal of the benzyl group in the usual way and purification by chromatography provided the title compound as a mixture of diastereomers. [α]D25 =-4.04° (c=1, methanol).

Workup

  1. customRemoval of the benzyl group
  2. customin the usual way and purification by chromatography

Sources & evidence

ORD record
ord-f5282b269af4496fb176721b5249d416
Source dataset
uspto-grants-1985_11
Patent number
US04552889

Reaction notes

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