| Identification | More | [Name]
N-Cbz-L-serine methyl ester | [CAS]
1676-81-9 | [Synonyms]
CBZ-L-SERINE METHYL ESTER
CBZ-SER-OME
N-ALPHA-CARBOBENZOXY-L-SERINE METHYL ESTER
N-CARBOBENZOXY-L-SERINE METHYL ESTER
N-CARBOBENZYLOXY-L-SERINE METHYL ESTER
N-CBZ-L-SERINE METHYL ESTER
n-z-l-serine methyl ester
Z-L-SERINE METHYL ESTER
Z-SERINE-OME
Z-SER-OME
N-Benzyloxycarbonyl-L-serine methyl ester
Z-L-SER-OME
(S)-METHYL 2-(BENZYLOXYCARBONYLAMINO)-3-HYDROXYPROPANOATE
(S)-3-Hydroxy-2-(benzyloxycarbonylamino)propionic acid methyl ester
[(S)-3-Hydroxy-1-oxo-1-methoxypropan-2-yl]carbamic acid benzyl ester | [EINECS(EC#)]
605-484-2 | [Molecular Formula]
C12H15NO5 | [MDL Number]
MFCD00077039 | [Molecular Weight]
253.25 | [MOL File]
1676-81-9.mol |
| Chemical Properties | Back Directory | [Melting point ]
41-43 °C(lit.) | [Boiling point ]
170 °C0.01 mm Hg(lit.) | [density ]
1.2499 (rough estimate) | [refractive index ]
-15 ° (C=1, MeOH) | [Fp ]
>230 °F
| [storage temp. ]
-15°C | [solubility ]
Chloroform, Methanol | [form ]
Viscous Liquid or Solid | [pka]
10.49±0.46(Predicted) | [color ]
Pale yellow | [Optical Rotation]
-13.4°(C=0.01 g/ml MEOH) | [CAS DataBase Reference]
1676-81-9(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
Clear Waxy Solid | [Uses]
N-[(Phenylmethoxy)carbonyl]-L-serine Methyl Ester is used to inhibit the activity of Mycobacterium tuberculosis in studies. Also used in the synthesis of pyrazinecarboxamide-based compounds acting as inhibitors of diacylglycerol acetyltransferases regarding treatment of obesity. | [Uses]
N-Cbz-L-serine methyl ester is used to inhibit the activity of Mycobacterium tuberculosis in studies. Also used in the synthesis of pyrazinecarboxamide-based compounds acting as inhibitors of diacylglycerol acetyltransferases regarding treatment of obesity.
| [reaction suitability]
reaction type: solution phase peptide synthesis | [Synthesis]
To a suspension of L-serine methyl ester hydrochloride (1.00 g, 6.43 mmol, 1.00 equiv) in dioxane (5.00 mL) was added an aqueous solution (25.7 mL) of NaHCO3 (1.62 g, 19.3 mmol, 3.00 equiv). Subsequently, a dioxane solution (15.0 mL, diluted with 4.20 mL dioxane) of benzyl chloroformate (Cbz-Cl, 1.10 mL, 7.72 mmol, 1.20 eq.) was added to the reaction system and the reaction was stirred at 25 °C. After 5 hours of reaction, the reaction was quenched with 1 M HCl aqueous solution and the aqueous layer was extracted with ethyl acetate (2×). The organic layers were combined, washed with 10% NaCl aqueous solution, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: hexane solution of 50% ethyl acetate) to afford N-benzyloxycarbonyloxy-L-serine methyl ester (1.50 g, 5.92 mmol, 92% yield) as a colorless oil. | [References]
[1] Journal of Organic Chemistry, 1996, vol. 61, # 16, p. 5528 - 5531
[2] Organic and Biomolecular Chemistry, 2015, vol. 13, # 26, p. 7177 - 7192
[3] Synthesis, 1996, # 2, p. 189 - 191
[4] Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 106 - 110
[5] Organic Letters, 2018, vol. 20, # 4, p. 1019 - 1022 |
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