L-(+)-Cysteine → HCID 87461492, compound

HRID 504072Notes

Reaction equation

HRID 504072 reaction equation
C(=O)(O)[O-].[Na+].[NH2:6][C@H:7]([C:10]([OH:12])=[O:11])[CH2:8][SH:9].[CH3:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][C:17]=1[OH:23])=O>O>[OH:23][C:17]1[CH:18]=[C:19]([OH:22])[CH:20]=[CH:21][C:16]=1[CH2:14][CH2:13][NH:6][C@H:7]([C:10]([OH:12])=[O:11])[CH2:8][SH:9]

Participants

5

Reactant 3

HCID 5862L-(+)-CysteineHCID 69902',4'-DihydroxyacetophenoneHCID 516892Sodium Bicarbonate

Product 1

HCID 87461492HCID 87461492, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ingredients. (1) Water 97.3 (2) Sodium Bicarbonate 0.9 (3) L-Cysteine 1.2 (4) Resacetophenone 1.5. Procedure. Mix (1) to (3). Heat to 70 to 80 C. Add (4). An instantaneous reaction occurs and a clear yellow solution is obtained. The mixing and heating is continued for 1 hour, and then hydrogenated over Pt catalyst. After filtration of catalyst, solution of N-[(2,4-dihydroxyphenyl)ethyl]cysteine Sodium in water is thus obtained, pH 8.5. Water is evaporated to ⅓ in volume and the solution allowed to cool. The pH is adjusted to 6.5 with citric acid (2.0 grams of 50% solution). N-[(2,4-dihydroxyphenyl)ethyl]cysteine is obtained as a pale, yellow solid.

Workup

  1. temperatureHeat to 70 to 80 C
  2. customAn instantaneous reaction
  3. customa clear yellow solution is obtained
  4. temperatureThe mixing and heating
  5. filtrationAfter filtration of catalyst, solution of N-[(2,4-dihydroxyphenyl)ethyl]cysteine Sodium in water
  6. customis thus obtained
  7. customWater is evaporated
  8. temperatureto cool

Sources & evidence

ORD record
ord-33eb8afcd5e04570a66aff4f17149ed7
Source dataset
uspto-grants-2010_08
Patent number
US07777073B2

Reaction notes

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