| Identification | More | [Name]
N-Carbobenzyloxy-L-threonine methyl ester | [CAS]
57224-63-2 | [Synonyms]
N-ALPHA-CARBOBENZOXY-L-THREONINE METHYL ESTER
N-CARBOBENZOXY-L-THREONINE METHYL ESTER
N-CARBOBENZYLOXY-L-THREONINE METHYL ESTER
Z-L-THREONINE METHYL ESTER
Z-THREONINE-OME
Z-THR-OME
L-Threonine, N-(phenylmethoxy)carbonyl-, methyl ester
CBZ-L-THREONINE METHYL ESTER
N-Carbobenzyloxy-L-threonine methyl ester, Z-L-Threonine methyl ester | [Molecular Formula]
C13H17NO5 | [MDL Number]
MFCD00038585 | [Molecular Weight]
267.28 | [MOL File]
57224-63-2.mol |
| Chemical Properties | Back Directory | [Appearance]
white to off-white powder | [Melting point ]
92-94 °C(lit.) | [alpha ]
-18 º (c=1, MeOH) | [Boiling point ]
410.46°C (rough estimate) | [density ]
1.2100 (rough estimate) | [refractive index ]
1.4365
| [storage temp. ]
-15°C | [form ]
Powder | [pka]
10.79±0.46(Predicted) | [color ]
White | [Optical Rotation]
[α]25/D 18°, c = 1 in methanol | [Water Solubility ]
miscible | [BRN ]
2220800 | [Major Application]
peptide synthesis | [InChI]
1S/C13H17NO5/c1-9(15)11(12(16)18-2)14-13(17)19-8-10-6-4-3-5-7-10/h3-7,9,11,15H,8H2,1-2H3,(H,14,17)/t9-,11+/m1/s1 | [InChIKey]
OPZWAOJFQFYYIX-KOLCDFICSA-N | [SMILES]
COC(=O)[C@@H](NC(=O)OCc1ccccc1)[C@@H](C)O | [CAS DataBase Reference]
57224-63-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Safety Statements ]
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Chemical Properties]
white to off-white powder | [Uses]
peptide synthesis | [reaction suitability]
reaction type: solution phase peptide synthesis | [Synthesis]
In a 2L beaker, 100 g of L-threonine methyl ester hydrochloride was dissolved in 600 ml of water and the pH was adjusted to a suitable range using sodium bicarbonate. Subsequently, 110 g of benzyl chloroformate (Z-Cl) was slowly added dropwise and the pH of the reaction system was kept between 8-9, which was adjusted using 2 M sodium hydroxide solution. After completion of the reaction, 1 L of ethyl acetate was added for extraction. The organic phase was washed sequentially with 500 ml of water and 500 ml of saturated saline, and then dried with 100 g of anhydrous sodium sulfate. After filtration, it was concentrated to dryness under reduced pressure to obtain a solid product. The solid was dissolved in 600 ml of a suitable solvent for crystallization, filtered and dried to give 140 g of N-benzyloxycarbonyl-L-threonine methyl ester (Z-Thr-OMe) in 89.1% yield. | [References]
[1] Patent: CN106631900, 2017, A. Location in patent: Paragraph 0015
[2] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 24, p. 3697 - 3703
[3] Justus Liebigs Annalen der Chemie, 1962, vol. 656, p. 190 - 204
[4] Journal of Organic Chemistry, 1985, vol. 50, # 23, p. 4515 - 4523
[5] Patent: WO2010/17060, 2010, A1. Location in patent: Page/Page column 44-45 |
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