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 | [CAS DataBase Reference]
57224-63-2(CAS DataBase Reference) |
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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