N-Cbz-L-serine methyl ester CAS 1676-81-9
N-Cbz-L-serine methyl ester Basic information
| Product Name: | N-Cbz-L-serine methyl ester |
| Synonyms: | N-CARBOBENZOXY-L-SERINE METHYL ESTER;N-CARBOBENZYLOXY-L-SERINE METHYL ESTER;N-CBZ-L-SERINE METHYL ESTER;CBZ-L-Serine methyleester;methyl ((benzyloxy)carbonyl)-L-serinate;L-Serine, N-[(phenylmethoxy)carbonyl]-, methyl ester;Z-Ser-OMe (Syrup);(2S)-3-hydroxy-2-(phenylmethoxycarbonylamino)propanoic acid methyl ester |
| CAS: | 1676-81-9 |
| MF: | C12H15NO5 |
| MW: | 253.25 |
| EINECS: | 605-484-2 |
| Product Categories: | Amino Acids;Amino Acids (N-Protected);Biochemistry;Cbz-Amino Acids;Amino Acid Derivatives;Peptide Synthesis;Serine |
| Mol File: | 1676-81-9.mol |
N-Cbz-L-serine methyl ester Chemical Properties
| 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. | Keep in dark place,Sealed in dry,Room Temperature |
| solubility | Chloroform, Methanol |
| pka | 10.49±0.46(Predicted) |
| form | Viscous Liquid or Solid |
| color | Pale yellow |
| Optical Rotation | -13.4°(C=0.01 g/ml MEOH) |
| CAS DataBase Reference | 1676-81-9(CAS DataBase Reference) |
Safety Information
| Safety Statements | 24/25 |
| WGK Germany | 3 |
| HS Code | 29242990 |
| Chemical Properties | Clear Waxy Solid |
| 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. |
| 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. |
| reaction suitability | reaction type: solution phase peptide synthesis |
| Synthesis | 5680-80-8 501-53-1 1676-81-9 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 |
N-Cbz-L-serine methyl ester Preparation Products And Raw materials
| Raw materials | Methanol-->N-Cbz-L-Serine-->L-Serine methyl ester hydrochloride-->L-SERINE METHYL ESTER-->Benzyl chloroformate-->Iodomethane-->Water-->Sodium bicarbonate-->1,4-Dioxane |
| Preparation Products | L-SERINE METHYL ESTER-->(S)-BENZYL 4-FORMYL-2,2-DIMETHYLOXAZOLIDINE-3-CARBOXYLATE-->(S)-3-BENZYL 4-METHYL 2,2-DIMETHYLOXAZOLIDINE-3,4-DICARBOXYLATE |
