HCID 44317006, compound → HCID 54561947, compound

HRID 1583128Notes

Reaction equation

HRID 1583128 reaction equation
[SH:1][CH2:2][CH2:3][C:4]([N:6]1[CH2:10][CH2:9][CH2:8][C@@H:7]1[C:11]([OH:13])=[O:12])=[O:5]>ClCCl>[C:11]([C@H:7]1[CH2:8][CH2:9][CH2:10][N:6]1[C:4](=[O:5])[CH2:3][CH2:2][S:1][S:1][CH2:2][CH2:3][C:4]([N:6]1[CH2:10][CH2:9][CH2:8][C@@H:7]1[C:11]([OH:13])=[O:12])=[O:5])([OH:13])=[O:12]

Participants

3

Reactant 1

HCID 44317006HCID 44317006, compound

Product 1

HCID 54561947HCID 54561947, compoundYield 8.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.9 g (4 mmol) 1-(3-mercapto-propionyl)-(R)-pyrrolidine-2-carboxylic acid (raw material) were dissolved in dichloromethane and extracted with 50 ml of an saturated aqueous solution of CuSO4. The aqueous phase was extracted twice with dichloromethane, the combined organic phases filtered, dried with magnesiumsulfate and evaporated. Chromatography with dichloromethane/acetone/formic acid 80/20/1 gave 70 mg (R)-1-[3-[3-[(R)-2-carboxy-pyrrolidin-1-yl]-3-oxo-propyldisulfanyl]-propionyl]-pyrrolidine-2-carboxylic acid as a colorless oil.

Workup

  1. extractionextracted with 50 ml of an saturated aqueous solution of CuSO4
  2. extractionThe aqueous phase was extracted twice with dichloromethane
  3. filtrationthe combined organic phases filtered
  4. dry with materialdried with magnesiumsulfate
  5. customevaporated

Sources & evidence

ORD record
ord-459cb6f46ab8446d8d72e09f54e5d2ba
Source dataset
uspto-grants-2004_05
Patent number
US06740760B2

Reaction notes

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