Synthesis of Benzyl (2-Aminoethyl)carbamate

Example 152

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To a solution of ethane-1,2-diamine (30.0 g, 0.5 mol, 10.0 eq.) in anhydrous DCM (500 mL) at 0° C. was added CbzCl (8.53 g, 0.050 mol, 1.0 eq.) in anhydrous DCM (250 mL) over 7 h. The reaction was then warmed to r.t. and stirred overnight. The mixture was washed with water and brine, dried over anhydrous Na₂SO₄, and concentrated to give benzyl (2-aminoethyl)carbamate as a white solid (7.0 g, 94% yield). ESI m/z calcd for C₁₀H₁₄N₂O₂[M+H]⁺: 195.1, found: 195.2.

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US11873281B2. Conjugates of cell binding molecules with cytotoxic agents (2024-01-16). HANGZHOU DAC BIOTECH CO., LTD. [CN], None [US], None [CN], None [CN]. Inventors: R. Yongxin Zhao [US], Yue Zhang [CN], Yourang Ma [CN].

Patent 2024

Brine Carbamate Diamine Ethane Synthesis

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Variable analysis

independent variables

Addition of CbzCl (8.53 g, 0.050 mol, 1.0 eq.) in anhydrous DCM (250 mL) over 7 h to a solution of ethane-1,2-diamine (30.0 g, 0.5 mol, 10.0 eq.) in anhydrous DCM (500 mL) at 0° C.

dependent variables

Formation of benzyl (2-aminoethyl)carbamate as a white solid (7.0 g, 94% yield)

control variables

Temperature of the reaction mixture (0° C, then warmed to r.t.)
Anhydrous reaction conditions (anhydrous DCM)

Annotations

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