Cysteamine Hydrochloride → HCID 86760071, compound

HRID 1824682Notes

Reaction equation

HRID 1824682 reaction equation
C(=O)(O)[O-].[Na+].Cl.[NH2:7][CH2:8][CH2:9][SH:10].[C:11]([O:15][C:16](=[O:25])[NH:17][C@@H:18]([C:22](F)=[O:23])[CH:19]([CH3:21])[CH3:20])([CH3:14])([CH3:13])[CH3:12]>C(Cl)Cl>[C:11]([O:15][C:16](=[O:25])[NH:17][C@@H:18]([C:22](=[O:23])[NH:7][CH2:8][CH2:9][SH:10])[CH:19]([CH3:20])[CH3:21])([CH3:12])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 9082Cysteamine HydrochlorideHCID 516892Sodium BicarbonateHCID 86760072HCID 86760072, compound

Product 1

HCID 86760071HCID 86760071, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 50 mL round-bottom flask charged with a solution of sodium bicarbonate (1 74.0 mg, 2.07 mmol) in 10.1 mL was added 2-aminoethanethiol hydrochloride (126.6 mg, 1.11 mmol). To this stirring solution was added dropwise over 60 seconds a solution of 25f (222.2 mg, 1.0 mmol) in 10.1 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 195.2 mg (71% from 24f) of clean 26f as a white solid. FTIR (film) 3289, 1687, 1645 cm −1.

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-5e1ab48615b94cfbbe28c01cc54a9762
Source dataset
uspto-grants-2006_05
Patent number
US07045360B2

Reaction notes

Loading…