DL-cysteine → 3-Dodecylmercapto-2-aminopropionic acid

HRID 466959Notes

Reaction equation

HRID 466959 reaction equation
[OH-].[Na+].[NH2:3][CH:4]([C:7]([OH:9])=[O:8])[CH2:5][SH:6].[CH2:10](Br)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>C(O)C>[CH2:21]([S:6][CH2:5][CH:4]([NH2:3])[C:7]([OH:9])=[O:8])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH3:10]

Participants

5

Reactant 3

HCID 594DL-cysteineHCID 89191-BromododecaneHCID 14798Sodium Hydroxide

Product 1

HCID 204954283-Dodecylmercapto-2-aminopropionic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

16.5 g. (0.42 mole) solid sodium hydroxide are dissolved in 1600 ml. ethanol, mixed with a solution of 25 g. (0.21 mole) D,L-cysteine in 150 ml. ethanol and, after the dropwise addition of 60 ml. (0.25 mole) dodecyl bromide, stirred for 24 hours at ambient temperature. The precipitate is then filtered off with suction, washed with ethanol and dissolved in water. After acidification with 4N hydrochloric acid, the precipitate is filtered off after 2 hours at 5° C. Yield 48.2 g. (81% of theory); m.p. 215°-218° C. (decomp.).

Workup

  1. filtrationThe precipitate is then filtered off with suction
  2. washwashed with ethanol
  3. dissolutiondissolved in water
  4. filtrationAfter acidification with 4N hydrochloric acid, the precipitate is filtered off after 2 hours at 5° C

Sources & evidence

ORD record
ord-f0b11c0e4fb745f09eddf6e93bf9de04
Source dataset
uspto-grants-1992_10
Patent number
US05158942

Reaction notes

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