Cysteamine Hydrochloride → HCID 86760073, compound

HRID 1824684Notes

Reaction equation

HRID 1824684 reaction equation
C(=O)(O)[O-].[Na+].Cl.[NH2:7][CH2:8][CH2:9][SH:10].[C:11]([O:15][C:16](=[O:26])[NH:17][C@@H:18]([C:23](F)=[O:24])[C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:14])([CH3:13])[CH3:12]>O.C(Cl)Cl>[C:11]([O:15][C:16](=[O:26])[NH:17][C@@H:18]([C:23](=[O:24])[NH:7][CH2:8][CH2:9][SH:10])[C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 3

HCID 9082Cysteamine HydrochlorideHCID 516892Sodium BicarbonateHCID 86760074HCID 86760074, compound

Product 1

HCID 86760073HCID 86760073, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a 25 mL round-bottom flask charged with a solution of sodium bicarbonate (83.0 mg, 0.99 mmol) in 4.8 mL water was added 2-aminoethanethiol hydrochloride (60.3 mg, 0.53 mmol). To this stirring solution was added dropwise over 60 seconds a solution of 25h (112.6 mg, 0.48 mmol) in 4.8 mL CH2Cl2. The reaction was vigorously stirred for 25 minutes at room temperature, then extracted twice with fresh CH2Cl2. The combined CH2Cl2 extracts were washed once with 5% aqueous HCl, once with 10% aqueous sodium bicarbonate, then once with water. The organic fraction was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford 26h as a colorless oil.

Workup

  1. extractionextracted twice with fresh CH2Cl2
  2. washThe combined CH2Cl2 extracts were washed once with 5% aqueous HCl, once with 10% aqueous sodium bicarbonate
  3. dry with materialThe organic fraction was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-696bc6e8d0744c119cf657c60d404175
Source dataset
uspto-grants-2006_05
Patent number
US07045360B2

Reaction notes

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