| Identification | More | [Name]
BOC-SER(ME)-OH | [CAS]
51293-47-1 | [Synonyms]
BOC-L-SERINE(METHYL ETHER)
BOC-O-METHYL-L-SER
BOC-O-METHYL-L-SERINE
BOC-O-METHYL-L-SERINE DCHA
BOC-O-METHYL-L-SERINE DICYCLOHEXYLAMMONIUM SALT
BOC-(S)-2-AMINO-3-METHOXYLPROPANOIC ACID
BOC-(S)-2-AMINO-3-METHOXYPROPIONIC ACID
BOC-SERINE(ME)-OH DCHA
BOC-SER(ME)-OH
BOC-SER(ME)-OH DCHA
N-ALPHA-T-BOC-O-METHYL-L-SERINE
N-ALPHA-T-BUTOXYCARBONYL-O-METHYL-L-SERINE
N-ALPHA-T-BUTOXYCARBONYL-O-METHYL-L-SERINE DICYCLOHEXYLAMMONIUM SALT
(S)-N-BOC-2-AMINO-3-METHOXY-PROPIONIC ACID
Boc-O-methyl-L-Serinedicyclohexylamine salt
Boc-O-Methyl-L-Se
N-tert-Butoxycarbonyl-O-methyl-L-serine | [EINECS(EC#)]
809-876-6 | [Molecular Formula]
C9H17NO5 | [MDL Number]
MFCD00153314 | [Molecular Weight]
219.23 | [MOL File]
51293-47-1.mol |
| Chemical Properties | Back Directory | [Boiling point ]
355.8±37.0 °C(Predicted) | [density ]
1.148±0.06 g/cm3(Predicted) | [storage temp. ]
-15°C
| [form ]
solid | [pka]
3.52±0.10(Predicted) | [color ]
Yellow-brown | [InChI]
InChI=1S/C9H17NO5/c1-9(2,3)15-8(13)10-6(5-14-4)7(11)12/h6H,5H2,1-4H3,(H,10,13)(H,11,12)/t6-/m0/s1 | [InChIKey]
RFGMSGRWQUMJIR-LURJTMIESA-N | [SMILES]
C(O)(=O)[C@H](COC)NC(OC(C)(C)C)=O | [CAS DataBase Reference]
51293-47-1(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
White to off-white crystals | [Uses]
BOC-SER(ME)-OH, also known as Boc-Ser-OMe or N-tert-butyloxycarbonyl-L-serine methyl ester, is an amino acid derivative commonly used in peptide synthesis. | [Synthesis]
General procedure for the synthesis of N-Boc-O-methyl-L-serine from O-methyl DL-serine and di-tert-butyl dicarbonate: 35 mL of aqueous 1 N sodium hydroxide solution and 35 mL of tetrahydrofuran (THF) were added to 2.0 g (17 mmol) of O-methyl DL-serine. With stirring at 0 °C, a solution of di-tert-butyl dicarbonate (4.03 g, 18.5 mmol) in THF (15 mL) was added slowly. The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the reaction mixture was concentrated by evaporation under reduced pressure. The aqueous phase was acidified to pH 4-5 with 10% aqueous citric acid and then extracted with ethyl acetate. The organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give 3.6 g of N-Boc-O-methyl-L-serine (98% yield). Mass spectrum (ESI) m/z: 220.1 (M + H)+. | [References]
[1] Chemistry - A European Journal, 2011, vol. 17, # 15, p. 4183 - 4194
[2] Patent: WO2016/11088, 2016, A2. Location in patent: Paragraph 00238; 00239 |
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