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ChemicalBook CAS DataBase List Fmoc-Pro-OH
71989-31-6

Fmoc-Pro-OH synthesis

5synthesis methods
To a solution of (S)-pyrrolidine-2-carboxylic acid (1 g, 8.7 mmol) in 1,4-dioxane (4 mL) and water (15 mL), K2CO3 (3.24 g, 23 mmol) was added, followed by the addition of 9-fluorenylmethyl chloroformate (2.3 g, 8.3 mmol). The resulting mixture was stirred overnight at room temperature and then treated with water (10 mL). The resulting mixture was extracted with diethyl ether (2 x 20 mL), and the aqueous phase was made acidic with 1M HCl to a pH of 2-3, followed by extraction with dichloromethane (3 x 50 mL). The combined organic layers were dried using anhydrous sodium sulfate and concentrated to yield Fmoc-Pro-OH as a white solid in a 95% yield (2.8 g).
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Yield:71989-31-6 95%

Reaction Conditions:

with potassium carbonate in 1,4-dioxane;water at 0 - 20;

Steps:

17.A Step A: (S)-1-((( 9H-fluoren-9-yl)methoxy)carbonyl)pyrrolidine-2-carboxylic acid
To a solution of (5')-pyrrolidine-2-carboxylic acid (1 g, 8.7 mmol) in 1,4-dioxane (4 mL) and H20 (15 mL) was added K2C03 (3.24 g, 23 mmol) followed by (9H-fluoren-9-yl)methyl chloroformate (2.3 g, 8.3 mmol) at 0 °C. The mixture was stirred at r.t. overnight and treated by H20 (10 mL). The resulting mixture was extracted with Et20 (2 x 20 mL). The aqueous phase was acidified with aq. HC1 (1 M) to pH=2-3, and extracted with DCM (3 x 50 mL). The combined organic layers were dried over anhydrous a2S04 and concentrated to give the desired product as a white solid (2.8 g, 95% yield). MS: 338 (M+l)+.

References:

AGIOS PHARMACEUTICALS, INC.;Popovici-Muller, Janeta;SAUNDERS, Jeffrey, O.;SALITURO, Francesco, G.;CAI, Zhenwei;YAN, Shunqi;ZHOU, Ding WO2013/107405, 2013, A1 Location in patent:Page/Page column 95

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