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 activity

[α]20/D 48°, c = 1 in H2O

Water Solubility 

miscible

Sensitive 

Hygroscopic

BRN 

3598081

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)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/38-36/37/38-22

Safety Statements 

22-24/25-37/39-26-36/37/39

WGK Germany 

3

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

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

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