Ethane, 2-bromo-1,1-diethoxy- → (2S)-2-(2',2'-Diethyloxyethylamino)-3-phenylpropionic Acid Ethyl Ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6])[CH3:2].[CH2:15]([O:17][CH:18]([O:21][CH2:22][CH3:23])[CH2:19]Br)[CH3:16].CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:14])[C@@H:5]([NH:6][CH2:19][CH:18]([O:21][CH2:22][CH3:23])[O:17][CH2:15][CH3:16])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2]Participants
6
Conditions
- Temperature
- 23 °C
Procedure
A solution of L-phenylalanine ethyl ester (8.37 g, 46.8 mmol, 1 equiv), bromoacetaldehyde diethyl acetal (10.6 mL, 70.1 mmol, 1.5 equiv), and DIEA (16.2 mL, 93.4 mmol, 2.0 equiv) in DMF (100 mL) was heated at 80° C. for 2 d. The resulting solution was cooled to 23° C., taken up in chloroform (200 mL), washed with 10% aqueous potassium carbonate (3×50 mL), dried over potassium carbonate, and concentrated. Purification of the residue by silica gel chromatography yield 7.4 g (54%) of product. 1H NMR (CDCl3) δ 1.13-1.23 (m, 9H), 2.61 (dd, 1H, J=11.8, 5.9), 2.78 (dd, 1H, J=11.8, 5.9), 2.96-3.03 (m, 2H), 3.46-3.53 (m, 1H), 3.55-3.70 (m, 4H), 4.18 (q, 2H, J=7.1), 4.57 (t, 1H, J=5.5), 7.19-7.33 (m, 5H).
Workup
- washwashed with 10% aqueous potassium carbonate (3×50 mL)
- dry with materialdried over potassium carbonate
- concentrationconcentrated
- customPurification of the residue by silica gel chromatography yield 7.4 g (54%) of product
Sources & evidence
- ORD record
- ord-bb85b7954dfc4a649cbc2ad645df7638
- Source dataset
- uspto-grants-2003_02
- Patent number
- US06514997B2
Reaction notes
Loading…