| Identification | More | [Name]
BOC-TRANS-4-FLUORO-L-PROLINE | [CAS]
203866-14-2 | [Synonyms]
(2S,4R)-4-FLUORO-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER
BOC-TRANS-4-FLUORO-L-PROLINE
N-BOC-(4S,2R)-4-FLUORO-2-PYRROLIDINECARBOXYLIC ACID
N-BOC-TRANS-4-FLUORO-L-PROLINE
N-T-BOC-TRANS-4-FLUORO-L-PROLINE
N-(TERT-BUTOXYCARBONYL)-(2S,4R)-4-FLUOROPROLINE
(2R,4S)-N-Boc-trans-4-Fluoro-D-proline methyl ester
(2S,4R)-N-Boc-trans-4-Fluoro-L-Proline
(2S,4R)-4-Fluoropyrrolidine-2-carboxylic acid, N4-BOC protected
trans-4-Fluoro-L-proline, N-BOC protected
(2S,4R)-Boc-4-fluoro-pyrrolidine-2-carboxylic acid
(2R,4S)-N-BOC-4-FLUORO-D-PROLINE
(2S,4R)-4-Fluoropyrrolidine-2-carboxylic acid, N-BOC protected
(2S,4R)-1-(tert-Butoxycarbonyl)-4-fluoro-2-pyrrolidinecarboxylic Acid
(2S,4R)-1-Boc-4-fluoro-2-pyrrolidinecarboxylic Acid
N-(tert-Butoxycarbonyl)-trans-4-fluoro-L-proline | [Molecular Formula]
C10H16FNO4 | [MDL Number]
MFCD06796085 | [Molecular Weight]
233.24 | [MOL File]
203866-14-2.mol |
| Questions And Answer | Back Directory | [Synthesis]
Step 1) Synthesis of Compound 9-2 Compound 9-1 (11.0 g, 44.8 mmol) was dissolved in DCM (200 mL). Et2NSF3 (8.85 mL, 67.3 mmol) was slowly added dropwise at -78 °C. After the addition was complete, the reaction was kept at a constant temperature for 2.0 hours, and then reacted at room temperature for 19 hours. After the reaction was complete, ammonium chloride aqueous solution (100 mL) was added to quench the reaction. The aqueous layer was extracted with DCM (100 mL × 3). The organic phases were combined, washed with saturated brine, dried over anhydrous Na2SO4, concentrated, and purified by column chromatography (eluent: PE/EtOAc(v/v) = 20/1) to obtain 7.75 g of pale yellow liquid, yield: 70%. Step 2) Synthesis of compound 9-3 Compound 9-2 (5.83 g, 23.6 mmol) was dissolved in THF (30 mL). At 0 °C, an aqueous solution of lithium hydroxide (1.98 g, 30 mL) was slowly added dropwise. After the addition was complete, the reaction was allowed to proceed at room temperature for 2.0 hours. After the reaction was complete, the pH of the reaction solution was adjusted to 5 with dilute hydrochloric acid (1M). After removing THF, the pH of the aqueous layer was adjusted to 2 with dilute hydrochloric acid (1M). The solution was extracted with EtOAc (80mL×3). The organic phases were combined, washed with saturated brine, dried over anhydrous Na2SO4, and concentrated to give 5.27g of white solid. Yield: 96%. |
| Chemical Properties | Back Directory | [Melting point ]
115-119°C | [Boiling point ]
346.0±42.0 °C(Predicted) | [density ]
1.24±0.1 g/cm3(Predicted) | [refractive index ]
-69 ° (C=1, MeOH) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
soluble in Methanol | [form ]
powder to crystal | [pka]
3.53±0.40(Predicted) | [color ]
White to Almost white | [Optical Rotation]
[α]22/D -65.0±5°, c = 1 in chloroform | [InChI]
InChI=1S/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 | [SMILES]
N1(C(OC(C)(C)C)=O)C[C@H](F)C[C@H]1C(O)=O | [CAS DataBase Reference]
203866-14-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P264-P271-P280-P302+P352-P305+P351+P338 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
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 | [HazardClass ]
IRRITANT | [HS Code ]
29339900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
White powder | [Uses]
N-Boc-trans-4-fluoro-L-proline is a useful synthetic intermediate. It is used to prepare potent 3- or 4-substituted-2-cyanopyrrolidine dipeptidyl peptidase IV inhibitors. It is also used to synthesize pyrrolotriazines derivatives as pan-Aurora kinase inhibitors and anti-tumor agents. |
|
| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
Alfa Aesar
|
| Telephone: |
400-6106006 |
| Website: |
http://chemicals.thermofisher.cn |
| Company Name: |
Energy Chemical
|
| Telephone: |
400-0056266 |
| Website: |
www.energy-chemical.com |
|