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| | L-Proline benzyl ester hydrochloride Basic information |
| | L-Proline benzyl ester hydrochloride Chemical Properties |
| Melting point | 148-151 °C(lit.) | | alpha | -44 º (c=1, methanol) | | refractive index | 1.4365 | | storage temp. | Inert atmosphere,Room Temperature | | solubility | soluble in Methanol | | form | Crystalline Powder | | color | White to pale yellow | | Optical Rotation | [α]20/D 48°, c = 1 in H2O | | Water Solubility | miscible | | Sensitive | Hygroscopic | | BRN | 3598081 | | Major Application | peptide synthesis | | InChI | InChI=1/C12H15NO2.ClH/c14-12(11-7-4-8-13-11)15-9-10-5-2-1-3-6-10;/h1-3,5-6,11,13H,4,7-9H2;1H/t11-;/s3 | | InChIKey | NEDMOHHWRPHBAL-MERQFXBCSA-N | | SMILES | [C@@H]1(NCCC1)C(=O)OCC1=CC=CC=C1.Cl |&1:0,r| | | CAS DataBase Reference | 16652-71-4(CAS DataBase Reference) |
| | L-Proline benzyl ester hydrochloride Usage And Synthesis |
| Chemical Properties | White powder | | Uses | L-Proline Benzyl Ester Hydrochloride acts as a reagent in the synthesis and bioactivity of a goralatide analog with anti-leukemic activity. | | reaction suitability | reaction type: solution phase peptide synthesis | | Synthesis | Under nitrogen protection, benzyl alcohol (70 mL, 651 mmol) was cooled to 0 °C and thionyl chloride (7.0 mL, 91.2 mmol) was added slowly and dropwise. L-proline (5.0 g, 43.4 mmol) was then added, and the reaction system was kept stirred at 0 °C and under nitrogen atmosphere for 2 hours. The temperature was slowly increased to room temperature and stirring was continued for 48 hours. Upon completion of the reaction, the reaction mixture was slowly poured into ether (300 mL) and left to crystallize at -20°C for 7 days. The resulting white solid precipitate was collected by filtration, washed with ether and dried under vacuum to give L-proline benzyl ester hydrochloride (9.88 g, 93% yield). The product characterization data were as follows: melting point 142.1-144.0 °C (literature value: 143-144 °C); 1H NMR (300 MHz, CDCl3): δ 7.41-7.21 (m, 5H), 5.16 (s, 2H), 3.80 (dd, J = 3.83, 5.9 Hz, 1H), 3.15-3.01 (m, 1H), 3.00-2.82 (m, 1H), 2.42-2.21 (m, 1H), 2.13 (dd, J = 12.9, 7.5 Hz, 1H), 1.92-1.62 (m, 3H); 13C NMR (75 MHz, CDCl3): δ 175.5, 136.0, 128.8, 128.5, 128.3, 66.9, 59.9, 47.2, 30.4, 25.6. Elemental analysis (C12H16ClNO2) calculated values: C, 59.63; H, 6.67; N, 5.79; measured values: C, 59.50; H, 6.86; N, 5.64. | | References | [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 15, p. 5056 - 5060
[2] Tetrahedron, 2010, vol. 66, # 29, p. 5384 - 5395
[3] Patent: CN105061283, 2017, B. Location in patent: Paragraph 0030-0032; 0045-0047; 0057
[4] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1959, p. 1851; engl. Ausg. S. 1768, 1769
[5] Journal of Biological Chemistry, 1951, vol. 193, p. 97,108 |
| | L-Proline benzyl ester hydrochloride Preparation Products And Raw materials |
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