Cysteamine Hydrochloride → HCID 53633136, compound

HRID 1824677Notes

Reaction equation

HRID 1824677 reaction equation
C(=O)(O)[O-].[Na+].Cl.[NH2:7][CH2:8][CH2:9][SH:10].[C:11]([O:15][C:16](=[O:22])[NH:17][CH2:18][C:19](F)=[O:20])([CH3:14])([CH3:13])[CH3:12]>O.C(Cl)Cl>[C:11]([O:15][C:16](=[O:22])[NH:17][CH2:18][C:19](=[O:20])[NH:7][CH2:8][CH2:9][SH:10])([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 3

HCID 9082Cysteamine HydrochlorideHCID 516892Sodium BicarbonateHCID 11095182HCID 11095182, compound

Product 1

HCID 53633136HCID 53633136, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a 50 mL round-bottom flask charged with a solution of sodium bicarbonate (141 mg, 1.68 mmol) in 8.2 mL water was added 2-aminoethanethiol hydrochloride (102.5 mg, 0.90 mmol). To this stirring solution was added dropwise over 60 seconds a solution of 25a (145.6 mg, 0.82 mmol) in 8.2 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 132.8 mg (69% from 24a) of clean 26a 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-8fe6a509922f459d9fd577fa94422e18
Source dataset
uspto-grants-2006_05
Patent number
US07045360B2

Reaction notes

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