| Identification | Back Directory | [Name]
N-Trityl-L-serine methyl ester | [CAS]
4465-44-5 | [Synonyms]
Trt-Ser-OMe
Trt-L-Ser-Ome
(diphenylMethyl)benzene
(4S)-4-aMinooxolan-3-one
Methyl trityl-L-serinate
N-TRITYL-L-SERINE METHYL ESTER
-Methyl 3-hydroxy-2-(tritylamino)
N-Trityl-L-serine methyl ester 99%
N-(TriphenylMethyl)-L-serine Methyl Ester
N-Trityl-L-serine Methyl Ester
Trt-Ser-OMe
L-Serine, N-(triphenylmethyl)-, methyl ester
(S)-methyl 3-hydroxy-2-(tritylamino)propanoate
methyl (2S)-3-hydroxy-2-(tritylamino)propanoate
N-(Triphenylmethyl)-L-serine methyl ester, 97.5%
methyl (2S)-3-hydroxy-2-[(triphenylmethyl)amino]propanoate
N-(Triphenylmethyl)-L-serine Methyl Ester | [Molecular Formula]
C23H23NO3 | [MDL Number]
MFCD00192570 | [MOL File]
4465-44-5.mol | [Molecular Weight]
361.43 |
| Chemical Properties | Back Directory | [Melting point ]
148-150 °C(lit.)
| [alpha ]
31 º (c=1 in methanol) | [Boiling point ]
538.2±50.0 °C(Predicted) | [density ]
1.169±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
soluble in Methanol | [form ]
powder to crystal | [pka]
14.01±0.10(Predicted) | [color ]
White to Light yellow | [Optical Rotation]
[α]20/D +31°, c = 1 in methanol | [InChI]
InChI=1S/C23H23NO3/c1-27-22(26)21(17-25)24-23(18-11-5-2-6-12-18,19-13-7-3-8-14-19)20-15-9-4-10-16-20/h2-16,21,24-25H,17H2,1H3/t21-/m0/s1 | [InChIKey]
LXAWQKKSNNYYEK-NRFANRHFSA-N | [SMILES]
C(OC)(=O)[C@H](CO)NC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 |
| Hazard Information | Back Directory | [Uses]
peptide synthesis | [reaction suitability]
reaction type: solution phase peptide synthesis | [Synthesis]
A solution of dichloromethane (CH2Cl2, 40 mL) with triethylamine (Et3N, 13.4 mL, 96.78 mmol) was slowly added dropwise to a dichloromethane (CH2Cl2, 129 mL) containing L-serine methyl ester hydrochloride (5.0 g, 32.26 mmol) and triphenylmethane chloride (Ph3CCl, 13.5 g, 48.39 mmol) solution and the reaction was carried out at 0 °C under the protection of nitrogen (N2). Subsequently, the reaction system was gradually warmed up to room temperature with continuous stirring overnight. Upon completion of the reaction, the reaction was quenched with saturated sodium bicarbonate (NaHCO3) solution and the aqueous phase was extracted with dichloromethane (CH2Cl2). The organic phases were combined, washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to afford N-trityl-L-serine methyl ester as a colorless solid (11.41 g, 98% yield). | [References]
[1] Acta Chemica Scandinavica, 1994, vol. 48, # 6, p. 511 - 516
[2] Patent: WO2007/68474, 2007, A1. Location in patent: Page/Page column 51; 52
[3] Patent: WO2016/8946, 2016, A1. Location in patent: Page/Page column 101
[4] Angewandte Chemie - International Edition, 2017, vol. 56, # 40, p. 12245 - 12249
[5] Angew. Chem., 2017, vol. 129, p. 12413 - 12417,5 |
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