3-hydroxy-2-[(3-phenyl-2-phenylmethoxycarbonylamino-propanoyl)amino]propanoic acid synthesis

8synthesis methods

Product Name:3-hydroxy-2-[(3-phenyl-2-phenylmethoxycarbonylamino-propanoyl)amino]propanoic acid
CAS Number:860-55-9
Molecular formula:C20H22N2O6
Molecular Weight:386.3985

56-45-1 Synthesis

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L-Phenylalanine, N-[(phenylmethoxy)carbonyl]-, anhydride with ethyl hydrogen carbonate

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3-hydroxy-2-[(3-phenyl-2-phenylmethoxycarbonylamino-propanoyl)amino]propanoic acid

860-55-9
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Yield:860-55-9 158 mg

Reaction Conditions:

with sodium hydrogencarbonate in tetrahydrofuran;water at 0; for 0.5 h;

Steps:

A Typical Procedure of the Amidation of Cbz-L-Phenylalanine (6a) Using Ethyl Chloroformate is as Follows.

General procedure: To acolorless solution of 150 mg (0.50 mmol) of Cbz-L-phenylalanine (6a) in 10 mL of THF were added at 0 °C 67 L (0.70mmol, 1.4 equiv) of ethyl chloroformate and 209 L (1.5 mmol,3.0 equiv) of triethylamine. After stirring for 30 min at 0 °C, asolution of 110 mg (0.75 mmol, 1.5 equiv) of L-Glu-OH (2e)and 63 mg (0.75 mmol, 1.5 equiv) of NaHCO3 in 10 mL of H2Owas added at 0 °C to the colorless suspension. The mixture wasstirred for 30 min at 0 °C and the resulting colorless clear solution was concentrated in vacuo. The residue was adjusted topH 2 by addition of a 1.0 M aqueous solution of HCl. Thecolorless suspension was diluted with 10 mL of brine, extractedwith 25 ml 3 of a 4:1 mixture of EtOAc and MeOH, anddried over anhydrous MgSO4. The crude product was chromatographed on silica gel with a 9:1 mixture of chloroform andMeOH containing 1% AcOH to afford 187 mg (87% yield) ofCbz-L-Phe-L-Glu-OH (7ae).Cbz-L-Phe-L-Ser-OH (7aa): 158 mg (82%), colorlesspowder; mp; 156159 °C; 30 D = +4.82 (c 1.00, MeOH); 1H NMR (400 MHz, MeOD-d 4): 2.85 (dd, J = 9.8, 13.8 Hz,1H, CHAC6H5), 3.19 (dd, J = 4.7, 13.8 Hz, 1H, CHBC6H5), 3.83(dd, J = 3.8, 11.2 Hz, 1H, CHAOH), 3.92 (dd, J = 4.5, 11.2 Hz,1H, CHBOH), 4.46 (dd, J = 4.7, 9.8 Hz, 1H, CHCH2C6H5), 4.48(dd, J = 3.8, 4.5 Hz, 1H, CHCH2OH), 4.98 (d, J = 12.6 Hz, 1H,OCHAC6H5), 5.03 (d, J = 12.6 Hz, 1H, OCHBC6H5), 7.197.33(m, 10H, C6H5 2); 13C NMR (100 MHz, MeOD-d 4): 39.2,56.2, 57.8, 63.0, 67.6, 127.8, 128.7, 129.0, 129.5, 129.5, 130.4,138.2, 138.6, 158.4, 173.1, 174.2; HRMS (ESI-TOF): Calcd forC20H23N2O6 (M+H)+: 387.1551, found: 387.1539; IR (KBr,νmax/cm1): 3298 (OH), 1732 (CO2), 1647 (CON).

References:

Ezawa, Tetsuya;Jung, Seunghee;Kawashima, Yuya;Noguchi, Takuya;Imai, Nobuyuki [Bulletin of the Chemical Society of Japan,2017,vol. 90,# 6,p. 689 - 696]

56-45-1 Synthesis

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