Cysteamine Hydrochloride → (2R)-2-{[(tert-butoxy)carbonyl]amino}-2-phenylacetic acid

HRID 1824686Notes

Reaction equation

HRID 1824686 reaction equation
C(=O)(O)[O-:2].[Na+].Cl.NCCS.[C:11]([O:15][C:16](=[O:28])[NH:17][C@@H:18]([C:25](F)=[O:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:14])([CH3:13])[CH3:12]>O.C(Cl)Cl>[C:11]([O:15][C:16]([NH:17][C@H:18]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:25]([OH:2])=[O:26])=[O:28])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 9082Cysteamine HydrochlorideHCID 516892Sodium BicarbonateHCID 14824294HCID 14824294, compound

Product 1

HCID 2755953(2R)-2-{[(tert-butoxy)carbonyl]amino}-2-phenylacetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a 50 mL round-bottom flask charged with a solution of sodium bicarbonate (78.0 mg, 0.93 mmol) in 4.5 mL water was added 2-aminoethanethiol hydrochloride (56.6 mg, 0.50 mmol). To this stirring solution was added dropwise over 60 seconds a solution of 25j (114.8 mg, 0.45 mmol) in 4.5 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 132.3 mg (86% from 24j) of 26j as an off-white paste.

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-aa0af6aac06b404fbb814970e13563fb
Source dataset
uspto-grants-2006_05
Patent number
US07045360B2

Reaction notes

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