N-Boc-(2S,4R)-4-fluoro-2-pyrrolidinecarboxylic acid

N-Boc-(2S,4R)-4-fluoro-2-pyrrolidinecarboxylic acid - Names and Identifiers

Name	N-Boc-trans-4-fluoro-L-proline
Synonyms	Boc-Trans-4-Fluoro-L-Proline BOC-TRANS-4-FLUORO-L-PROLINE N-Boc-trans-4-fluoro-L-proline N-BOC-TRANS-4-FLUORO-L-PROLINE N-T-BOC-TRANS-4-FLUORO-L-PROLINE (2S,4R)-N-Boc-trans-4-Fluoro-L-Proline trans-4-Fluoro-L-proline, N-BOC protected N-(TERT-BUTOXYCARBONYL)-(2S,4R)-4-FLUOROPROLINE N-BOC-(4S,2R)-4-FLUORO-2-PYRROLIDINECARBOXYLIC ACID N-Boc-(2S,4R)-4-fluoro-2-pyrrolidinecarboxylic acid (2S,4R)-4-Fluoropyrrolidine-2-carboxylic acid, N4-BOC protected (2S,4R)-1-tert-butoxycarbonyl-4-fluoro-pyrrolidine-2-carboxylic acid
CAS	203866-14-2
InChI	InChI=1/C10H16FNO4/c1-10(2,3)16-9(15)12-5-6(11)4-7(12)8(13)14/h6-7H,4-5H2,1-3H3,(H,13,14)/t6-,7+/m1/s1
InChIKey	YGWZXQOYEBWUTH-RQJHMYQMSA-N

N-Boc-(2S,4R)-4-fluoro-2-pyrrolidinecarboxylic acid - Physico-chemical Properties

Molecular Formula	C10H16FNO4
Molar Mass	233.24
Density	1.24±0.1 g/cm3(Predicted)
Melting Point	115-119°C
Boling Point	346.0±42.0 °C(Predicted)
Flash Point	163°C
Solubility	soluble in Methanol
Vapor Presure	1.05E-05mmHg at 25°C
Appearance	powder to crystal
Color	White to Almost white
pKa	3.53±0.40(Predicted)
Storage Condition	Inert atmosphere,Room Temperature
Refractive Index	-69 ° (C=1, MeOH)
MDL	MFCD06796085

N-Boc-(2S,4R)-4-fluoro-2-pyrrolidinecarboxylic acid - Risk and Safety

Hazard Symbols	Xi - Irritant
Risk Codes	36/37/38 - Irritating to eyes, respiratory system and skin.
Safety Description	S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37 - Wear suitable protective clothing and gloves.
WGK Germany	3
HS Code	29339900
Hazard Class	IRRITANT

N-Boc-(2S,4R)-4-fluoro-2-pyrrolidinecarboxylic acid - Reference Information

application

(2R,4S)-N-BOC-4-fluoro-D-proline is a pharmaceutical intermediate, which can be made of N-Boc-trans-4-hydroxy-L-proline methyl ester as raw material, first fluoro to obtain N-Boc-trans-4-fluoro-L-proline methyl ester, and then hydrolyze the methyl ester to obtain (2R,4S)-N-BOC-4-fluorine-D-proline. (2R,4S)-N-BOC-4-fluorine-D-proline can be used to prepare NS5A inhibitor.

preparation

step 1) synthesis of compound 9-2 compound 9-1(11.0g,44.8mmol) is dissolved in DCM(200mL), Et2NSF3
(8.85mL,67.3mmol) is slowly dropped at -78 ℃, after dropping, after constant temperature reaction for 2.0 hours, reaction at room temperature for 19 hours. After the reaction is complete, ammonium chloride
aqueous solution (100mL) is added to quench the reaction, the water layer is extracted with DCM(100mL × 3), organic phase is combined, saturated salt water is washed, anhydrous
Na2SO4 is dried, concentrated and purified by column chromatography (eluent: PE/EtOAc(v/v)= 20/1) to obtain light yellow liquid
7.75g, yield: 70%. Step 2) Synthesis of Compound 9-3 Dissolve compound 9-2(5.83g,23.6mmol) in THF(30mL), slowly drop lithium hydroxide water
solution (1.98g,30mL) at 0 ℃, drop it and react at room temperature for 2.0 hours. After the reaction is complete, adjust the pH value of the reaction solution with dilute hydrochloric acid (1M)
to 5. after THF is removed, adjust the pH value to 2 with dilute hydrochloric acid (1M), extract with EtOAc(80mL × 3), combine the organic phase, wash with
saturated salt water, dry with anhydrous Na2SO4, concentrate to obtain 5.27g of white solid with a yield of 96%.

Last Update：2024-04-09 20:52:54