| Identification | More | [Name]
N-BOC-cis-4-fluoro-L-proline | [CAS]
203866-13-1 | [Synonyms]
(2S,4S)-4-FLUORO-1-TERT-BUTOXYCARBONYL-PYRROLIDINE-2-CARBOXYLIC ACID
(2S,4S)-4-FLUORO-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER
(2S,4S)-BOC-4-FLUORO-PYRROLIDINE-2-CARBOXYLIC ACID
BOC-CIS-4-FLUORO-L-PROLINE
BOC-CIS-4-FLUORO-PRO-OH
N-T-BOC-CIS-4-FLUORO-L-PROLINE
N-TERT-BUTOXYCARBONYL-CIS-4-FLUORO-L-PROLINE
(2S,4S)-4-Fluoro-N-Boc-Pyrrolidine-2-carboxylic acid
N-Boc-cis-4-Fluoro-L-Proline
(2S,4S)-N-BOC-4-FLUORO-L-PROLINE
N-BOC-(4S,2S)-4-FLUORO-2-PYRROLIDINECARBOXYLICACID
(2S,4S)-1-(tert-Butoxycarbonyl)-4-fluoro-2-pyrrolidinecarboxylic Acid
(2S,4S)-1-Boc-4-fluoro-2-pyrrolidinecarboxylic Acid | [Molecular Formula]
C10H16FNO4 | [MDL Number]
MFCD04973957 | [Molecular Weight]
233.24 | [MOL File]
203866-13-1.mol |
| Chemical Properties | Back Directory | [Melting point ]
157-161.°C | [Boiling point ]
346.0±42.0 °C(Predicted) | [density ]
1.24±0.1 g/cm3(Predicted) | [refractive index ]
-57 ° (C=1, MeOH) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
powder to crystal | [pka]
3.53±0.40(Predicted) | [color ]
White to Almost white | [Optical Rotation]
[α]22/D 71.0±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-/m0/s1 | [InChIKey]
YGWZXQOYEBWUTH-BQBZGAKWSA-N | [SMILES]
N1(C(OC(C)(C)C)=O)C[C@@H](F)C[C@H]1C(O)=O | [CAS DataBase Reference]
203866-13-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [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 . | [WGK Germany ]
3 | [HazardClass ]
IRRITANT | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Chemical Properties]
White powder | [Uses]
N-Boc-cis-4-fluoro-L-proline can be used as a substrate in the preparation of:
- α4β2 Receptor ligands bearing pyrrolidine nucleus.
- β-Amino pyrrolidine-2-carbonitrile derivatives as possible dipeptidyl peptidase IV (DPP4) inhibitors.
| [Synthesis]
General procedure for the synthesis of (2S,4S)-4-fluoro-1-tert-butoxycarbonylpyrrolidine-2-carboxylic acid from N-tert-butoxycarbonyl-cis-4-fluoro-L-proline methyl ester: To a solution of N-tert-butoxycarbonyl-cis-4-fluoro-L-proline methyl ester (5.83 g, 23.58 mmol) in tetrahydrofuran (THF, 30 mL) was added, at 0 °C, lithium hydroxide (LiOH, 1.98 g) in aqueous solution (30 mL). The reaction mixture was stirred at room temperature for 2 h. The pH was subsequently adjusted to 5 with dilute hydrochloric acid (1 M). After evaporating THF under reduced pressure, the pH of the aqueous layer was adjusted to 2 with dilute hydrochloric acid (1 M) and extracted with ethyl acetate (EtOAc, 80 mL x 3). The organic layers were combined, dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure to afford (2S,4S)-4-fluoro-1-tert-butoxycarbonylpyrrolidine-2-carboxylic acid as a white solid (5.3 g, 96% yield). The structure of the compound was confirmed by the following spectral data: mass spectrum (ESI, positive ion mode) m/z: 234.24 [M + H]+; NMR hydrogen spectrum (400 MHz, CDCl3) δ (ppm): 8.76 (broad single peak, 1H), 5.28-5.12 (multiple peaks, 1H), 4.56-4.44 (multiple peaks, 1H), 3.86- 3.58 (multiple peaks, 2H), 2.77-2.01 (multiple peaks, 2H), 1.48-1.44 (double peaks, 9H, J = 16 Hz). | [References]
[1] Patent: WO2014/19344, 2014, A1. Location in patent: Paragraph 00435
[2] Patent: WO2014/82380, 2014, A1. Location in patent: Paragraph 00403; 00405
[3] Patent: WO2014/82379, 2014, A1. Location in patent: Page/Page column 144; 145
[4] Patent: WO2014/131315, 2014, A1. Location in patent: Page/Page column 144
[5] Patent: US2015/79028, 2015, A1. Location in patent: Paragraph 1061; 1066; 1067; 1068; 1069 |
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