Cysteamine Hydrochloride → HCID 87903836, compound

HRID 1824683Notes

Reaction equation

HRID 1824683 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]>O.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

6

Reactant 3

HCID 9082Cysteamine HydrochlorideHCID 516892Sodium BicarbonateHCID 10751345HCID 10751345, compound

Product 1

HCID 87903836HCID 87903836, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a 50 mL round-bottom flask charged with a solution of sodium bicarbonate (158.1 mg, 1.88 mmol) in 9.2 mL water was added 2-aminoethanethiol hydrochloride (114.7 mg, 1.01 mmol). To this stirring solution was added dropwise over 60 seconds a solution of 25g (201.3 mg, 0.92 mmol) in 9.2 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 222.0 mg (80% from 24g) of clean 26g as a colorless oil. FTIR (neat) 3300, 1681, 1652 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-8e88a74688c54a8fa47d402268293af5
Source dataset
uspto-grants-2006_05
Patent number
US07045360B2

Reaction notes

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