| Identification | More | [Name]
L-Alanine benzyl ester 4-toluenesulfonate | [CAS]
42854-62-6 | [Synonyms]
ALANINE-OBZL P-TOSYLATE
H-ALA-OBZL P-TOSYLATE
H-ALA-OBZL TOS
H-ALA-OBZL TOSOH
L-ALANINE BENZYL ESTER 4-TOLUENESULFONATE
L-ALANINE BENZYL ESTER 4-TOLUENESULFONATE SALT
L-ALANINE BENZYL ESTER P-TOLUENESULFONATE
L-ALANINE BENZYL ESTER P-TOLUENESULFONATE SALT
L-ALANINE BENZYL ESTER, P-TOLUENESULFONIC ACID SALT
L-ALANINE BENZYL ESTER P-TOLUENESULPHONATE
L-ALANINE BENZYL ESTER P-TOSYLATE
L-ALANINE BENZYL ESTER P-TOSYL ESTER
L-ALANINE BENZYL ESTER PTSA
L-ALANINE BENZYL ESTER TOLUENE-4-SULFONATE
L-ALANINE BENZYL ESTER TOSYLATE
L-ALA-OBZL TSOH
?-alaninebenzylesterp-toluenesulfonate,98%
L-Alanine benzyl ester Toluene Sulfonic acid
O-benzyl-L-alanine toluene-p-sulphonate
L-ALA-OBEL.TSOH | [EINECS(EC#)]
255-969-4 | [Molecular Formula]
C17H21NO5S | [MDL Number]
MFCD00066143 | [Molecular Weight]
351.42 | [MOL File]
42854-62-6.mol |
| Chemical Properties | Back Directory | [Appearance]
Yellowish Oil | [Melting point ]
112-116 °C | [alpha ]
-5 º (c=3% in methanol) | [refractive index ]
-5.0 ° (C=3, MeOH) | [storage temp. ]
0-6°C | [solubility ]
DMSO, Methanol | [form ]
Solid | [color ]
White | [Optical Rotation]
[α]20/D 5.0±0.5°, c = 3% in methanol | [Usage]
A benzoxazine derivatives as modulators of chemokine receptors for treatment of inflammatory and immunoregulatory diseases.
| [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 Data | Back Directory | [Risk Statements ]
36/37/38 | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [HS Code ]
29224999 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [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]
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 |
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