1,2-Dichloroethane → HCID 86622305, compound

Step A (1): DIEA (2.52 mL, 14.5 mmol) was added to a mixture of (S)-methyl 2-aminopent-4-enoate hydrochloride (500 mg, 3.03 mmol) [Del Valle, J. R.; Goodman, M. J. of Org. Chem. 2004, 69, 8946-8948], 2-propylpentanoic acid (417 mg, 2.89 mmol), EDC (581 mg, 3.03 mmol), and HOBt (409 mg, 3.03 mmol) in DMF (15 mL) at rt. The mixture was stirred for 18 h and subsequently poured into 200 mL 1M HCl. The aqueous layer was extracted with EtOAc/hexanes (95:5) (2×200 mL). The combined organic extracts were washed with brine, dried with MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography to give (S)-methyl 2-(2-propylpentanamido)pent-4-enoate 852 mg (quantitative yield) as a white solid. LC-MS (M+H)+=256.16. 1H NMR (500 MHz, CDCl3) δ 5.90 (s, 1H) 5.64-5.85 (m, 1H) 4.95-5.14 (m, 2H) 4.04 (dd, J=5.04, 2.29 Hz, 2H) 3.75 (s, 3H) 2.28-2.46 (m, 1H) 2.07-2.29 (m, 2H) 1.62-1.64 (m, 1H) 1.46-1.47 (m, 1H) 1.18-1.36 (m, 4H) 0.87 (t, J=6.87 Hz, 3H).

1. extractionThe aqueous layer was extracted with EtOAc/hexanes (95:5) (2×200 mL)
2. washThe combined organic extracts were washed with brine
3. dry with materialdried with MgSO4
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customThe residue was purified by silica gel chromatography

ORD record

ord-e8b19acaf4514b359a44a89290cb7aa8

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07772221B2