Pyridine → HCID 85876541, compound

HRID 1441219Notes

Reaction equation

HRID 1441219 reaction equation
[C:1](Cl)(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].N1C=CC=CC=1.ON1C(=O)CCC1=O.[NH2:31][CH2:32][CH2:33][SH:34]>O>[C:1]([NH:31][CH2:32][CH2:33][SH:34])(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6058CysteamineHCID 66986Myristoyl chlorideHCID 80170N-Hydroxysuccinimide

Product 1

HCID 85876541HCID 85876541, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

Myristoyl chloride (1.0 mmol) was added with vigorous string to ice-cooled dry pyridine (1.0 ml), and followed immediately by N-hydroxysuccinimide (1.5 mmol). The mixture was stirred for 4 h at ambient temperature (˜23° C.). 2-aminoethanethiol free base (1.1 mmol) was added as solid to the mixture and allowed to react for 6 h at ambient temperature, followed by 3 days at 4° C. The product was treated with water (5 ml), stirred for 1 h at ambient and filtered, washing with cold water. The white solid was dissolved in dimethylsulphoxide and reprecipitated with water and then vacuum dried over phosphorous pentoxide. The final yield was 0.21 g (˜70%). Thiol titration using Ellman's reagent indicated that the product contained ˜45% free thiol.

Workup

  1. customto react for 6 h at ambient temperature
  2. waitfollowed by 3 days at 4° C
  3. stirringstirred for 1 h at ambient and
  4. filtrationfiltered
  5. washwashing with cold water
  6. dissolutionThe white solid was dissolved in dimethylsulphoxide
  7. customreprecipitated with water
  8. dry with materialvacuum dried over phosphorous pentoxide

Sources & evidence

ORD record
ord-127ea22c25e346dc8ff7c231b1553294
Source dataset
uspto-grants-2010_02
Patent number
US07655617B2

Reaction notes

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