1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 66893747, compound

Temperature

0 °C

In a round bottom flask under argon was placed N-(benzyloxycarbonyl)-α-phosphonoglycine methyl ester (3.04 g, 9.16 mmol) in dichloromethane (10 mL) and cooled to 0° C. This mixture was treated dropwise with 1,8-diazabicyclo[5.4.0]undec-7-ene (1.20 mL, 7.94 mmol) and stirred at 0° C. for 20 min. A solution of 3-methyl-cyclobutanecarbaldehyde (600 mg, 6.11 mmol) in dichloromethane (5 mL) was then added. After the addition was complete the reaction was warmed to 25° C. and stirred overnight. The mixture was then concentrated in vacuo and dissolved in ethyl acetate (100 mL). The ethyl acetate layer was washed with a saturated aqueous ammonium chloride solution (2×50 mL), a saturated aqueous solution of sodium chloride (50 mL), dried over sodium sulfate and concentrated in vacuo with silica gel (3 g). Purification by Biotage flash chromatography (40M column, 20% ethyl acetate/hexanes) afforded (Z)-2-benzyloxycarbonylamino-3-(3-methyl-cyclobutyl)-acrylic acid methyl ester (693 mg, 38%) as a yellow viscous oil.

1. customIn a round bottom flask under argon was placed
2. additionAfter the addition
3. temperaturewas warmed to 25° C.
4. stirringstirred overnight
5. concentrationThe mixture was then concentrated in vacuo
6. dissolutiondissolved in ethyl acetate (100 mL)
7. washThe ethyl acetate layer was washed with a saturated aqueous ammonium chloride solution (2×50 mL)
8. dry with materiala saturated aqueous solution of sodium chloride (50 mL), dried over sodium sulfate
9. concentrationconcentrated in vacuo with silica gel (3 g)
10. customPurification by Biotage flash chromatography (40M column, 20% ethyl acetate/hexanes)

ORD record

ord-ba0029940a7641e184d408142a9d0075

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07741327B2