Sodium Chloride → 3-((tert-Butoxycarbonyl)amino)-4,4-difluorobutanoic acid

HRID 1903249

Reaction equation

HRID 1903249 reaction equation
Cl.[F:2][CH:3]([F:10])[CH:4]([NH2:9])[CH2:5][C:6]([OH:8])=[O:7].[C:11](OC([O-])=O)([O-])=O.[C:18](=[O:21])(O)[O-:19].[Na+].[Cl-].[Na+].O1[CH2:29][CH2:28][CH2:27]C1>O>[F:2][CH:3]([F:10])[CH:4]([NH:9][C:18]([O:19][C:28]([CH3:27])([CH3:29])[CH3:11])=[O:21])[CH2:5][C:6]([OH:8])=[O:7]

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 15238643PyrocarbonateHCID 714030983-Amino-4,4-difluorobutanoic acid hydrochloride

Product 1

HCID 204684533-((tert-Butoxycarbonyl)amino)-4,4-difluorobutanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4,4-difluoro-3-amino-butanoic acid, hydrochloride prepared as in Step C (0.702 g, 4 mM), ditertiobutyl dicarbonate (0.916 g, 4.2 mM), sodium bicarbonate (0.336 g, 4 mM) in tetrahydrofuran and water (6 ml of a 1:1 mixture) is heated at reflux for 48 hours. The resulting solution is saturated with sodium chloride and extracted three times with chloroform. The organic phase is dried over anhydrous magnesium sulfate, and the solvent evaporated in vacuo yielding a colorless oil.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 48 hours
  3. extractionextracted three times with chloroform
  4. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  5. customthe solvent evaporated in vacuo
  6. customyielding a colorless oil

Sources & evidence

ORD record
ord-e51cfa98c7f84b508c523cc99e55a595
Source dataset
uspto-grants-1984_03
Patent number
US04435425

Linked notes

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