Methyl L-leucinate hydrochloride CAS 7517-19-3
Methyl L-leucinate hydrochloride Basic information
| Product Name: | Methyl L-leucinate hydrochloride |
| Synonyms: | Methyl (2S)-2-aMino-4-Methylpentanoate hydrochloride;L-Leucine Methyl ester hydrochloride 98%;L-Leucine Methyl Ester Hydrochloride, 97+%;L-Leucine methyl ester hydrochloride99+%;Methyl L-leucite hydrochloride;Methyl L-Leucinate Hydrochloride,99%e.e.;(2S)-Methyl 2-amino-4-methylpentanoate hydrochloride;L-Leucine methyl·hydrochloric acid |
| CAS: | 7517-19-3 |
| MF: | C7H16ClNO2 |
| MW: | 181.66 |
| EINECS: | 231-375-0 |
| Product Categories: | Peptide Synthesis;Amino Acids;Leucine [Leu, L];Amino Acids and Derivatives;Amino Acid Methyl Esters;Amino Acids (C-Protected);Biochemistry;Amino hydrochloride;Protected Amino Acids;Amino Acid Derivatives;Leucine |
| Mol File: | 7517-19-3.mol |
Methyl L-leucinate hydrochloride Chemical Properties
| Melting point | 151-153 °C(lit.) |
| alpha | 20 º (c=4.5, MeOH) |
| refractive index | 13 ° (C=2, H2O) |
| storage temp. | Inert atmosphere,2-8°C |
| solubility | H2O: 50 mg/mL, clear, colorless |
| form | Crystals or Crystalline Powder |
| color | White |
| Optical Rotation | [α]22/D +13°, c = 2 in H2O |
| Water Solubility | soluble |
| Sensitive | Hygroscopic |
| BRN | 3595133 |
| Major Application | peptide synthesis |
| InChI | InChI=1/C7H15NO2.ClH/c1-5(2)4-6(8)7(9)10-3;/h5-6H,4,8H2,1-3H3;1H/t6-;/s3 |
| InChIKey | DODCBMODXGJOKD-UZHXKHNSNA-N |
| SMILES | [C@H](N)(CC(C)C)C(=O)OC.Cl |&1:0,r| |
| CAS DataBase Reference | 7517-19-3(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 22-24/25-36/37/39-27-26 |
| WGK Germany | 3 |
| HazardClass | IRRITANT |
| HS Code | 29224995 |
| Storage Class | 11 - Combustible Solids |
| Chemical Properties | Crystalline |
| Uses | L-Leucine methyl ester is a protected form of L-Leucine (L330110). L-Leucine is an essential amino acid that induces a sharp decrease in blood glucose levels in individuals with idiopathic familial hypoglycemia, but has no known effects on normal, healthy individuals. L-Leucine also acts as an Isoleucine (I820210) antagonist in the rat, causing delays in growth, and is a potential tumour promoter of bladder cancer. |
| reaction suitability | reaction type: solution phase peptide synthesis |
| Synthesis | 67-56-1 61-90-5 7517-19-3 Under ice bath conditions, 60 mL of methanol was added to a 100 mL round bottom flask. 4 mL of sulfoxide chloride (SOCl2) was added slowly and dropwise through a constant pressure dropping funnel (with a drying tube fitted at the top), while the resulting off-gas was absorbed using NaOH solution. After stirring the reaction mixture for 1 h, 8 mmol of L-leucine was added and stirring was continued for 30 min at room temperature. Subsequently, the reaction system was warmed up to 66 °C and the reaction was refluxed for 6 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) with an ethanol solution of 2% ninhydrin as the color developer until the raw material spot disappeared. After completion of the reaction, the solvent was removed by distillation under reduced pressure to give L-leucine methyl ester hydrochloride in 100% yield. |
| References | [1] Patent: US2014/206741, 2014, A1. Location in patent: Paragraph 0121 [2] Journal of Organic Chemistry, 2003, vol. 68, # 12, p. 5006 - 5008 [3] Synthetic Communications, 2010, vol. 40, # 8, p. 1161 - 1179 [4] Bulletin des Societes Chimiques Belges, 1991, vol. 100, # 1, p. 63 - 77 [5] Chemical Biology and Drug Design, 2012, vol. 79, # 2, p. 216 - 222 |
Methyl L-leucinate hydrochloride Preparation Products And Raw materials
| Raw materials | L-Leucine, N-(methoxycarbonyl)-, methyl ester-->Z-LEU-OME-->methyl L-leucinate-->L-Leucine hydrochloride-->BOC-L-Leucine-->Methanol-->L-Leucine |
| Preparation Products | N-Cbz-L-Leucine-->1H-Pyrrole-1-acetic acid, 2-formyl-α-(2-methylpropyl)-, methyl ester-->N-(2-Chloroacetyl)-L-leucine methyl ester-->1H-Pyrrole-1-acetic acid, 2-formyl-α-(2-methylpropyl)--->(R)-(+)-2-AMINO-4-METHYL-1,1-DIPHENYL-1-PENTANOL-->Z-VAL-LEU-OH |
