L-(+)-Cysteine → HCID 58681528, compound

HRID 1985793Notes

Reaction equation

HRID 1985793 reaction equation
[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][SH:4].Br[CH2:9][CH:10]1[CH2:12][CH2:11]1>[OH-].[Na+].O1CCOCC1>[NH2:1][C@@H:2]([CH2:3][S:4][CH2:9][CH:10]1[CH2:12][CH2:11]1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 2

HCID 5862L-(+)-CysteineHCID 81503Bromomethylcyclopropane

Product 1

HCID 58681528HCID 58681528, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

An ice water bath cooled solution of L-cysteine in 1N sodium hydroxide (740 mL) and dioxane (740 mL) was treated with bromomethylcyclopropane (50 g, 370 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 16 h. Dioxane was removed under reduced pressure and the resulting aqueous solution was adjusted to pH 6 with 6N HCl and placed in a refrigerator for 20 h. The product was collected by vacuum filtration, washed with hexanes and lyophilized to give 2(R)-amino-3-cyclopropylmethylsulfanylpropionic acid (57.28 g) as a white solid.

Workup

  1. customDioxane was removed under reduced pressure
  2. waitplaced in a refrigerator for 20 h
  3. filtrationThe product was collected by vacuum filtration
  4. washwashed with hexanes

Sources & evidence

ORD record
ord-fbe79bf65b664d59814891c06c23b496
Source dataset
uspto-grants-2009_06
Patent number
US07547701B2

Reaction notes

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