N-((1,1-dimethylethoxy)carbonyl)-beta-alanine → tert-Butyl (3-oxo-3-phenylpropyl)carbamate

HRID 2189921Notes

Reaction equation

HRID 2189921 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:14]1([Li])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1>[O:13]=[C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:10][CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 178506676HCID 178506676, compound

Product 1

HCID 17818960tert-Butyl (3-oxo-3-phenylpropyl)carbamateYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (−78° C.) solution of 3-(tert-butoxycarbonylamino)propanoic acid (1.0 g, 5.3 mmol) in THF (53 mL) was added phenyllithium (9.9 mL, 16 mmol, 1.6 M solution in cyclohexane/ether). After warming slowly to 0° C. and then stirring for 1 hour, the reaction mixture was quenched with saturated NH4Cl (10 mL), diluted with water (70 mL) and extracted with ether. The combined organics were washed with brine (80 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was chromatographed (20% ethyl acetate in hexanes) to provide the product (0.69 g, 59%) as yellow oil.

Workup

  1. customthe reaction mixture was quenched with saturated NH4Cl (10 mL)
  2. additiondiluted with water (70 mL)
  3. extractionextracted with ether
  4. washThe combined organics were washed with brine (80 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was chromatographed (20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-8ce7e1c3470a40e5a5aa7bd1a2a4c12c
Source dataset
uspto-grants-2012_12
Patent number
US08324257B2

Reaction notes

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