4-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of chloromethyl chlorosulfate (1.1 equivalent) and 4-tert-Butoxycarbonylamino-butyric acid (1 equivalent) was added NaHCO3 (3.6 equivalents) and Bu4NHSO4 (catalytic amount) in water/CH2Cl2 (1:1). The mixture was stirred at room temperature overnight. The organic phase was thereafter separated and the aqueous phase was extracted with CH2Cl2 (three times). The combined organic layer was washed with NaHCO3 (×3), brine (×3), dried with MgSO4, filtered and evaporated. The organic phase was thereafter separated the aqueous phase was extracted with CH2Cl2 (three times) The combined organic layer was washed with NaHCO3 (×3), brine (×3) dried with MgSO4 filtered evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of γ-aminobutyric acid (1 equivalent) in t-BuOH (4 ml/gram) and H2O (3 ml/gram) was added NaOH (1 equivalent), BOC2O (1 equivalent), and the mixture was stirred at room temperature for 24 hours. The solvent was thereafter evaporated and the residue was partitioned between hexane and water. The aqueous layer was acidified with KHSO41N to reach pH=2, and was thereafter extracted with CH2Cl2. The organic layer was dried over MgSO4 and the solvent was evaporated to give the desired product as a white solid (85% yield). The solvent was thereafter evaporated the residue was partitioned between hexane and water was thereafter extracted with CH2Cl2 The organic layer was dried over MgSO4 the solvent was evaporated