Water → HCID 25168940, compound

HRID 1525591Notes

Reaction equation

HRID 1525591 reaction equation
[C:1]([NH:4][C@H:5]([C:8]([OH:10])=[O:9])[CH2:6][SH:7])(=[O:3])[CH3:2].[P:11](Cl)(Cl)(Cl)=[O:12].[OH-:16].[Na+].[OH2:18]>>[C:1]([NH:4][C@H:5]([C:8]([OH:10])=[O:9])[CH2:6][S:7][P:11]([OH:12])([OH:18])=[O:16])(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 962WaterHCID 12035N-Acetyl-L-CysteineHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychloride

Product 1

HCID 25168940HCID 25168940, compound

Procedure

N-acetyl-S-phosphocysteine was synthesized according to the procedure followed by Binkely (1954). N-acetyl cysteine (0.5 g) was dissolved in 8 mL of distilled water in an ice bath. The NAC solution was then treated with 0.2 mL of phosphorus oxychloride and with sodium hydroxide to maintain the basic pH of 11. The resulting white solid was dried and re-dissolved in deuterium oxide for 31P, 13C and 1H NMR analysis. After analysis, the sample was dried, re-suspended in water, and treated with 1 mg (10 units) of alkaline phosphatase, and stirred for 2 hours. The solution was dried and resuspended in deuterium oxide for NMR analysis.

Workup

  1. temperatureto maintain the basic pH of 11
  2. customThe resulting white solid was dried
  3. dissolutionre-dissolved in deuterium oxide for 31P, 13C and 1H NMR analysis
  4. customAfter analysis, the sample was dried
  5. additiontreated with 1 mg (10 units) of alkaline phosphatase
  6. customThe solution was dried

Sources & evidence

ORD record
ord-16ed8f4456fd4cfa9a79e9b43f9802be
Source dataset
uspto-grants-2015_07
Patent number
US09084803B2

Reaction notes

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