L-(+)-Cysteine → HCID 15453674, compound

HRID 1985805Notes

Reaction equation

HRID 1985805 reaction equation
[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][SH:4].[F:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]Br)=[CH:11][CH:10]=1>[OH-].[Na+].O1CCOCC1>[NH2:1][C@@H:2]([CH2:3][S:4][CH2:13][C:12]1[CH:15]=[CH:16][C:9]([F:8])=[CH:10][CH:11]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 2

HCID 5862L-(+)-CysteineHCID 680214-Fluorobenzyl bromide

Product 1

HCID 15453674HCID 15453674, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

L-cysteine (15.97 g) was dissolved in a mixture of 1.0 M aqueous sodium hydroxide (265 mL) and 1,4-dioxane (265 mL). 4-Fluorobenzylbromide (24.85 g) was added dropwise over 30 min. After stirring overnight, dioxane was removed and the pH of the residual aqueous solution was adjusted to pH-6 with 3M hydrochloric acid. A white precipitate began to form immediately upon addition of the acid and additional water (150 mL) was added to aid stirring of the thick suspension. The reaction mixture was cooled to 0° C. for 1 h and the precipitates were collected by filtration and washed with cold water, Et2O, and hexane, and dried under high vacuum to give 2(R)-amino-3-(4-fluorobenzylsulfanyl)-propionic acid (28.68 g) as a white solid.

Workup

  1. customdioxane was removed
  2. customto form immediately upon addition of the acid and additional water (150 mL)
  3. additionwas added to aid
  4. stirringstirring of the thick suspension
  5. filtrationthe precipitates were collected by filtration
  6. washwashed with cold water, Et2O, and hexane
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-fa04f28cf2c444c59d361796b6abcf92
Source dataset
uspto-grants-2009_06
Patent number
US07547701B2

Reaction notes

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