N-(9-Fluorenylmethoxycarbonyloxy)succinimide → 3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-2,2-dimethylpropanoic acid

Participants

Reaction Steps

A solution of 3-amino-2,2-dimethylpropanoic acid hydrochloride (1.0 g, 6.5 mmol, 1.0 eq.) in 10 mL of 10% Na2CO3 was added to a solution of 1-{[(9H-fluoren-9-ylmethoxy)carbonyl]oxy}pyrrolidine-2,5-dione (2.3 g, 6.5 mmol, 1.0 eq.) in 10 mL of DME. The reaction was allowed to stir at room temperature overnight. Reaction was concentrated to a smaller volume and then washed two times with ether. The aqueous layer was acidified to pH<2 with concentrated HCl and then extracted three times with a 10% methanol 90% dichloromethane solution. The organics where combined before being washed with 1M HCl and brine. The organic layer was dried over sodium sulfate and concentrated in vacuo producing #124 (2.2 g, 98%) as a white solid. LC-MS (Protocol Q1): m/z 362.0 [M+Na+] retention time=0.89 minutes.

Provenance & Evidence