L-Alanine benzyl ester 4-toluenesulfonate CAS 42854-62-6
L-Alanine benzyl ester 4-toluenesulfonate Basic information
| Product Name: | L-Alanine benzyl ester 4-toluenesulfonate |
| Synonyms: | (S)-Benzyl 2-aminopropanoate 4-methylbenzenesulfonate;L-Alanine benzyl ester 4-toluenesulfonate salt≥ 99% (HPLC);L-Ala-OBzl·TosOH;ALANINE-OBZL P-TOSYLATE;H-Ala-OBzlos (Alanine benzyl ester para toluene sulfonate);L-ALANINE BENZYL ESTER 4-TOLUENESULFONATE;L-ALANINE BENZYL ESTER 4-TOLUENESULFONATE SALT;L-ALANINE BENZYL ESTER P-TOLUENESULFONATE |
| CAS: | 42854-62-6 |
| MF: | C17H21NO5S |
| MW: | 351.42 |
| EINECS: | 255-969-4 |
| Product Categories: | Amino Acid Derivatives;Amino Acids & Derivatives;Aromatics;Chiral Reagents;Alanine;Peptide Synthesis;Alanine [Ala, A];Amino Acids and Derivatives;Amino Acids;Amino Acids Derivatives;Amino Acids 13C, 2H, 15N;Amino Acid Benzyl Esters;Amino Acids (C-Protected);Biochemistry |
| Mol File: | 42854-62-6.mol |
L-Alanine benzyl ester 4-toluenesulfonate Chemical Properties
| Melting point | 112-116 °C |
| alpha | -5 º (c=3% in methanol) |
| refractive index | -5.0 ° (C=3, MeOH) |
| storage temp. | Inert atmosphere,Room Temperature |
| solubility | DMSO, Methanol |
| form | Solid |
| color | White |
| Optical Rotation | [α]20/D 5.0±0.5°, c = 3% in methanol |
| BRN | 3586474 |
| Major Application | peptide synthesis |
| InChI | InChI=1/C10H13NO2.C7H8O3S/c1-8(11)10(12)13-7-9-5-3-2-4-6-9;1-6-2-4-7(5-3-6)11(8,9)10/h2-6,8H,7,11H2,1H3;2-5H,1H3,(H,8,9,10)/t8-;/s3 |
| InChIKey | NWOPHJSSBMABBD-JNODIIHCNA-N |
| SMILES | C1(S(=O)(=O)O)=CC=C(C)C=C1.C1(=CC=CC=C1)COC(=O)[C@@H](N)C |&1:21,r| |
| CAS DataBase Reference | 42854-62-6(CAS DataBase Reference) |
Safety Information
| Risk Statements | 36/37/38 |
| Safety Statements | 22-24/25-44-35-28-26-7-4 |
| WGK Germany | 3 |
| HS Code | 29224999 |
| Storage Class | 11 - Combustible Solids |
| Chemical Properties | Yellowish Oil |
| Uses | A benzoxazine derivatives as modulators of chemokine receptors for treatment of inflammatory and immunoregulatory diseases. |
| reaction suitability | reaction type: solution phase peptide synthesis |
| Synthesis | 56-41-7 104-15-4 100-51-6 42854-62-6 To a 300 mL three-necked flask equipped with a thermometer, stirring device, and Dean-Stark separator were added 5.00 g (56.12 mmol) L-alanine, 41.03 g (379.42 mmol) benzyl alcohol, and 12.81 g (67.34 mmol) p-toluenesulfonic acid. The system pressure was reduced from atmospheric pressure (101.3 kPa) to 2.0 kPa. The reaction mixture was heated to an internal temperature of about 50 °C to start azeotropic removal of water and slowly warmed up to 62 °C over a period of 2 hours. Maintaining the same pressure and temperature, the reaction was continued with stirring for 3.5 hours. The reaction solution was cooled to 50 °C and 111.66 g of tert-butyl methyl ether was added dropwise over 30 minutes and about 0.005 g (0.01 mmol) of L-alanine benzyl ester p-toluenesulfonate was added as a crystal seed. After keeping stirring at 50°C for 30 minutes, 55.83 g of tert-butyl methyl ether was continued dropwise over 1 hour. Stirring was continued at 50 °C for 1 h, followed by slow cooling to 0 °C over 5 h and stirring at 0 °C overnight. The crystals were collected by filtration and washed with 15.00 g of pre-cooled tert-butyl methyl ether in three portions. Drying gave 18.26 g of L-alanine benzyl ester p-toluenesulfonate in 98.6% yield based on L-alanine. The optical purity of the product was ≥99.9% e.e. |
| References | [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 2, p. 339 - 345 [2] Patent: EP2062873, 2009, A1. Location in patent: Page/Page column 6 [3] Amino Acids, 2017, vol. 49, # 5, p. 965 - 974 [4] Patent: US2016/97052, 2016, A1. Location in patent: Paragraph 0308 [5] Journal of Antibiotics, 1998, vol. 51, # 8, p. 786 - 794 |
L-Alanine benzyl ester 4-toluenesulfonate Preparation Products And Raw materials
| Raw materials | L-Alanine-->p-Toluenesulfonic acid-->Benzyl alcohol |
| Preparation Products | N-[(S)-(+)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanine-->BOC-VAL-ALA-OBN |
