ChemicalBook CAS DataBase List Fmoc-Pro-OH

Fmoc-Pro-OH synthesis

5synthesis methods

Product Name:Fmoc-Pro-OH
CAS Number:71989-31-6
Molecular formula:C20H19NO4
Molecular Weight:337.37

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).

28920-43-6
550 suppliers
$5.00/5g

147-85-3 Synthesis

147-85-3
1083 suppliers
$6.00/25g

71989-31-6
535 suppliers
$6.00/5g

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

FullText

82911-69-1 Synthesis