ChemicalBook CAS DataBase List DL-THREO-2-ACETAMIDO-L-(4-NITROPHENYL)-L,3-PROPANEDIOL

DL-THREO-2-ACETAMIDO-L-(4-NITROPHENYL)-L,3-PROPANEDIOL synthesis

8synthesis methods

Product Name:DL-THREO-2-ACETAMIDO-L-(4-NITROPHENYL)-L,3-PROPANEDIOL
CAS Number:4423-58-9
Molecular formula:C11H14N2O5
Molecular Weight:254.24

Benzoic acid, 2-[(4-methylphenyl)methoxy]-, methyl ester

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DL-THREO-2-ACETAMIDO-L-(4-NITROPHENYL)-L,3-PROPANEDIOL

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Yield:4423-58-9 90%

Reaction Conditions:

with sodium hydrogencarbonate in tetrahydrofuran;water at 0 - 20;

Steps:

2

Example 2: Synthesis of Compounds 1-3, 3-2, and 3-7; N-[2-Hydroxy-l-hydroxymethyl-2-(4-nitro-phenyl)-ethyl]-acetamide (2): To a mixture of Z)-(-)-threo-2-amino-^-nitrophenyl-propane-l,3-diol (1) (9.85 g, 46.4 mmol), NaHC0₃ (29.2 g, 348.0 mmol), water (300 ml) and THF (100 ml) was added dropwise a solution of acetic anhydride (13.1 ml, 139.1 mmol) in THF (30 ml) at 0 °C. After addition was completed, the resulted mixture was stirred at room temperature overnight. The reaction mixture was extracted with EtOAc (300 ml x 3). The EtOAc extract was washed with brine (100 ml), dried over Na₂S0 and concentrated. The crude product was triturated with EtOAc (30 ml) and filtered. The solid was collected and dried to afford 2 as white powder (10.6 g, 90%). 'NMR (300 MHz, DMSO-i?): δ 8.17 (d, J = 8.7 Hz, 2H), 7.58 (d, J = 8.7 Hz, 2H), 5.82 (d, J = 7.5 Hz, 1H), 5.01 (m, 1 H), 4.84 (t, J = 4.5 Hz, 1H), 3.94 (m, 1H), 3.53 (m, 1H), 3.28 (m, 1 H), 1.69 (s, 3H); Ci iH,₄N₂0₅, LCMS (EI) m/z: 254 (M⁺).

References:

WO2012/125832,2012,A2 Location in patent:Page/Page column 75-76