| Identification | More | [Name]
L-Proline benzyl ester hydrochloride | [CAS]
16652-71-4 | [Synonyms]
H-PRO-OBZL
H-PRO-OBZL HCL
L-PROLINE BENZYL ESTER
L-PROLINE BENZYL ESTER HCL
L-PROLINE BENZYL ESTER HYDROCHLORIDE SALT
L-PROLINE BENZYL ESTER MONOHYDROCHLORIDE
L-PYRROLIDINE-2-CARBOXYLIC ACID BENZYL ESTER HCL
PROLINE-OBZL HCL
PRO-OBZL HCL
TIMTEC-BB SBB003206
l-proline,phenylmethylester,hydrochloride
Proline benzyl ester hydrochloride
benzyl L-prolinate hydrochloride
L-PROLINE BENZYL ESTER HYDROCHLORIDE, 98 %
H-L-Pro-OBzl*HCl
L-Pro-OBzl.HCl | [EINECS(EC#)]
240-700-5 | [Molecular Formula]
C12H16ClNO2 | [MDL Number]
MFCD00039002 | [Molecular Weight]
241.71 | [MOL File]
16652-71-4.mol |
| Chemical Properties | Back Directory | [Appearance]
White powder | [Melting point ]
148-151 °C(lit.) | [alpha ]
-44 º (c=1, methanol) | [refractive index ]
1.4365
| [storage temp. ]
Store at RT. | [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) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P271-P280 | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/38:Irritating to eyes and skin .
R36/37/38:Irritating to eyes, respiratory system and skin .
R22:Harmful if swallowed. | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
3
| [HS Code ]
29339900 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [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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