L-(+)-Cysteine → HCID 53800139, compound
Reaction equation
[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][SH:4].[OH-].[Na+].[CH2:10]1[O:12][CH2:11]1>O>[OH:12][CH2:11][CH2:10][NH:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][SH:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
109.5 g (0.9 mol) L-cysteine was placed in a 2000 ml flask, and dissolved with 1000 ml water, to which was added 24 ml of 1 mol/l NaOH solution. In an ice bath, 96 ml (1.8 mol) ethylene oxide was slowly added dropwise into the cysteine solution. After stirring 1 h, the ice bath was removed and the mixture was warmed to room temperature and further reacted for 1 h. The reaction product was extracted with 1000 ml anhydrous ethyl ether for four times, while collecting the aqueous layers. The aqueous layers were evaporated to dryness obtaining a yellow crystal product. The yellow crystal product was recrystallized with water:ethanol=85 ml:350 ml, filtered, washed with 2000 ml of 95% ethanol, and dried obtaining 121.8 g of a white crystal product, yield 74.3%.
Workup
- customthe ice bath was removed
- customfurther reacted for 1 h
- extractionThe reaction product was extracted with 1000 ml anhydrous ethyl ether for four times
- customwhile collecting the aqueous layers
- customThe aqueous layers were evaporated to dryness
- customobtaining a yellow crystal product
- customThe yellow crystal product was recrystallized with water
- filtrationethanol=85 ml:350 ml, filtered
- washwashed with 2000 ml of 95% ethanol
- customdried
Sources & evidence
- ORD record
- ord-ef4f3088d34e40608c1c099994cb4a89
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08173643B2
Reaction notes
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