Sulfuric Acid → tert-butyl (2S)-2-amino-3-phenylpropanoate

HRID 1250126Notes

Reaction equation

HRID 1250126 reaction equation
OS(O)(=O)=O.[NH2:6][C@H:7]([C:15]([OH:17])=[O:16])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[Na+]>O1CCOCC1>[CH3:8][C:9]([O:16][C:15](=[O:17])[C@H:7]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[NH2:6])([CH3:14])[CH3:10]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6140L-PhenylalanineHCID 14798Sodium Hydroxide

Product 1

HCID 6931633tert-butyl (2S)-2-amino-3-phenylpropanoateYield 118%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

98% H2SO4 (7 mL; 0.13 mol) was dropped in 20 min in dioxane (70 mL), keeping temperature of the solution below 20° C. After addition of L-phenylalanine (commercial product) (16.5 g; 0.10 mol), the solution was stirred for 12 h at 132 kPa under isobutene atmosphere (commercial product) (absorbed 45 g; 0.80 mol). The solution was dropped in a mixture of ice (200 g) and 10 N NaOH (30 mL, 0.30 mol) and extracted with Et2O (1 L). After washing with H2O (150 mL), the organic phase was dried over Na2SO4 and evaporated under vacuum The residue was distilled, to obtain the desired product (13 g; 0.059 mol). Yield 59%.

Workup

  1. customtemperature of the solution below 20° C
  2. custom(commercial product) (absorbed 45 g; 0.80 mol)
  3. extractionextracted with Et2O (1 L)
  4. washAfter washing with H2O (150 mL)
  5. dry with materialthe organic phase was dried over Na2SO4
  6. customevaporated under vacuum The residue
  7. distillationwas distilled

Sources & evidence

ORD record
ord-094da04689694a2c8420bc77a07a753e
Source dataset
uspto-grants-2002_01
Patent number
US06337064B1

Reaction notes

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