| Identification | More | [Name]
D-Serine methyl ester hydrochloride | [CAS]
5874-57-7 | [Synonyms]
D-SERINE METHYL ESTER HYDROCHLORIDE
D-SERINE METHYL ESTER HYDROCHLORIDE SALT
D-SERINE-OME HCL
H-D-SER-OME HCL
METHYL D-SERINATE HYDROCHLORIDE
H-D-Ser-OMe.HCI
D-Ser-OMe.HCl
D-Serine Methyl Ester HCl
2-Amino-3-hydroxy-propionic Acid Methyl Ester Hydrochlorid
(R)-2-Amino-3-hydroxypropionic Acid Methyl Ester Hydrochloride
(R)-Methyl 2-Amino-3-hydroxypropanoate Hydrochloride | [EINECS(EC#)]
611-745-1 | [Molecular Formula]
C4H10ClNO3 | [MDL Number]
MFCD00066121 | [Molecular Weight]
155.58 | [MOL File]
5874-57-7.mol |
| Chemical Properties | Back Directory | [Appearance]
White Solid | [Melting point ]
163-166 °C(lit.)
| [alpha ]
-4 º (c=4 in ethanol) | [storage temp. ]
-15°C | [solubility ]
Soluble in ethanol and methanol. | [form ]
Liquid | [color ]
Clear colorless to yellow | [Optical Rotation]
[α]20/D 4°, c = 4 in ethanol | [Major Application]
peptide synthesis | [InChI]
InChI=1/C4H9NO3.ClH/c1-8-4(7)3(5)2-6;/h3,6H,2,5H2,1H3;1H/t3-;/s3 | [InChIKey]
NDBQJIBNNUJNHA-AENDTGMFSA-N | [SMILES]
[C@@H](N)(CO)C(=O)OC.Cl |&1:0,r| | [CAS DataBase Reference]
5874-57-7(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
White Solid | [Uses]
D-Serine Methyl Ester Hydrochloride (cas# 5874-57-7) is a compound useful in organic synthesis. | [reaction suitability]
reaction type: solution phase peptide synthesis | [Synthesis]
General procedure for the synthesis of D-serine methyl ester hydrochloride from methanol and D-serine:
4.2.1.1 Synthesis of methyl (R)-2-isopropyl-4,5-dihydrooxazole-4-carboxylate
First, sulfoxide chloride (SOCl?, 7.60 mL, 104.2 mmol) was slowly added dropwise to a methanolic solution of D-serine (10.0 g, 95.1 mmol) and the reaction mixture was stirred for 24 h at room temperature. After completion of the reaction, the solvent was removed by rotary evaporator to give a white solid. The solid was washed with hexane (3 x 25 mL) to give D-serine methyl ester hydrochloride (14.4 g, 97% yield) as a colorless solid. The product was characterized by 1H NMR (300 MHz, D?O) with the following chemical shifts: δ 4.32-4.28 (1H, m, CH), 4.12 (1H, dd, J = 4.2, 12.5 Hz, CHaHbOH), 4.02 (1H, dd, J = 3.4, 12.5 Hz, CHaHbOH), 3.88 (3H, s, CH?) . | [References]
[1] Journal of Organic Chemistry, 1997, vol. 62, # 2, p. 372 - 376
[2] Heterocyclic Communications, 2005, vol. 11, # 3-4, p. 343 - 346
[3] Journal of Medicinal Chemistry, 2010, vol. 53, # 15, p. 5716 - 5726
[4] Chemical Communications, 2016, vol. 52, # 55, p. 8612 - 8614
[5] Journal of Organic Chemistry, 2003, vol. 68, # 26, p. 10162 - 10165 |
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