Triethylamine → HCID 117995906, compound

Temperature

0 °C

To a suspension of 2,2′-[(2-{[6-(benzyloxy)-6-oxohexyl]amino}-2-oxoethyl)azanediyl]diacetic acid (1.0 g, 2.54 mmol) in CH2Cl2 (30 mL) at 0° C. was added trifluoroacetic anhydride (448 μL, 3.17 mmol). After stirring at 0° C. for 3 hr, the mixture was cooled to −30° C., to which a solution of Et3N (848 μL, 6.08 mmol) in DMF (20 mL) was added dropwise over 30 mins After stirring at −30° C. for 30 min, a mixture of 6-amino-N-{2-[(α-L-fucopyranosyl)oxy]ethyl}hexanamide (812 mg, 2.54 mmol) in DMF (30 mL) was added and the resulting mixture was allowed to stir at rt. After stirring for 16 hr, the mixture was concentrated and the residue was purified by flash chromatography on C18 reverse phase silica gel (42 g), eluting with 0-40% AcCN in water to produce the title compound. UPLC Method B: m/e=697.3876 [M+1]; Rt=3.398 min. 1H NMR (CD3OD) δ 1.23 (3 H, d, J=6.59), 1.39-1.36 (4 H, m), 1.56 (6 H, s), 1.67 (6 H, d, J=10.32), 2.23 (2 H, t, J=7.50), 2.41 (2 H, t, J=7.37), 3.24 (6 H, m), 3.42 (4 H, s), 3.49 (2 H, s), 3.57-3.52 (3 H, m), 3.68 (1 H, s), 3.77 (3 H, t, J=1.65), 3.98-3.94 (1 H, m), 4.77 (1 H, s), 5.14 (2 H, s), 7.38 (5 H, d, J=4.43).

1. additionwas added dropwise over 30 mins
2. stirringAfter stirring at −30° C. for 30 min
3. additionwas added
4. stirringto stir at rt
5. stirringAfter stirring for 16 hr
6. concentrationthe mixture was concentrated
7. customthe residue was purified by flash chromatography on C18 reverse phase silica gel (42 g)
8. washeluting with 0-40% AcCN in water

ORD record

ord-70959328fe2b4a3c8713620445638f9b

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09427475B2