Triethylamine → HCID 86699925, compound

Temperature

0 °C

In a round bottomed flask equipped with a magnetic stirrer and a dropping funnel (2R,3S)-3-hydroxy-2-[(4-methyltetrahydropyran-4-yl)oxycarbonylamino]-butanoic acid (0.2 g, 0.77 mmol) was dissolved in anhydrous CH2Cl2 (7 mL). The clear yellow solution was cooled to 0° C., PyBOP (0.48 g, 0.92 mmol) was added, followed by dropwise addition, over a period of 10 min, of Et3N (0.32 mL, 3.85 mmol) solution in anhydrous CH2Cl2 (5 mL). The crude mixture was stirred at 0° C. for 1 h then overnight at rt. The reaction was quenched by addition of 5% NaHCO3 solution (10 mL) and the corresponding mixture was vigorously stirred for 10 min. The two phases were separated and the organic one collected, dried over Na2SO4 and concentrated to dryness to leave an oil, which was purified by typical chromatography eluting with petroleum ether/AcOEt (from 20:80 to 0:100) to give title compound (0.036 g, 19%) as a light yellow oil. MS (ESI) m/z: 244.1 [M−H]+; (ESI) m/z: 242.2 [M−H]−. 1H NMR (DMSO-d6) δ 1.20 (d, J=6.3 Hz, 3H), 1.48 (s, 3H), 1.67 (m, 2H), 1.99 (m, 2H), 3.60 (m, 4H), 4.83 (m, 1H), 5.37 (dd, J=9.3, 6.3 Hz, 1H), 8.12 (d, J=9.3 Hz, 1H).

1. customovernight
2. customat rt
3. customThe reaction was quenched by addition of 5% NaHCO3 solution (10 mL)
4. customThe two phases were separated
5. customthe organic one collected
6. dry with materialdried over Na2SO4
7. concentrationconcentrated to dryness
8. customto leave an oil, which
9. customwas purified by typical chromatography
10. washeluting with petroleum ether/AcOEt (from 20:80 to 0:100)

ORD record

ord-81f00990d5414eec8e9371251c974979

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09353075B2