3-Butenoic acid → Methyl 3-(3-butenoyl)amino-3-phenylpropionate

HRID 1457716Notes

Reaction equation

[CH:1]([CH2:3][C:4](O)=[O:5])=[CH2:2].Cl.[NH2:8][CH:9]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:10][C:11]([O:13][CH3:14])=[O:12]>C(Cl)Cl>[C:4]([NH:8][CH:9]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:10][C:11]([O:13][CH3:14])=[O:12])(=[O:5])[CH2:3][CH:1]=[CH2:2]

Participants

Conditions

Temperature: -10 °C

Procedure

To a solution of vinylacetic acid (861 mg, 10.0 mmol), methyl 3-amino-3-phenylpropionate hydrochloride (2.37 g, 11.0 mmol) and TEA (1.6 mL, 12 mmol) in DCM (20 mL) at -10° C. was added DEC (2.11 g, 11.0 mmol). The resulting mixture was stirred at -10° C. for 15 hours. The mixture was then washed with water, 0.1M HCl, sat. NaHCO3, sat. NaCl and dried over anhydrous MgSO4. Concentration in vacuo followed by pumping until constant weight gave 2.36 g (95%) of the desired amide as a golden oil of suitable purity for further reaction; 1H NMR (300 MHz, CDCl3) 87.28 (m, 5H), 6.78 (bd, J=7.7 Hz, 1H), 5.95 (m, 1H), 5.43 (dt, J=8.4, 5.9 Hz, 1H), 5.25 (m, 2H), 3.61 (s, 3H), 3.04 (d, J=7.0 Hz, 2H), 2.88 (dq, J=15.0, 5.9 Hz, 2H).

Workup

washThe mixture was then washed with water, 0.1M HCl, sat. NaHCO3, sat. NaCl
dry with materialdried over anhydrous MgSO4
concentrationConcentration in vacuo

Sources & evidence

ORD record: ord-b7eb448bae744c2d9f8c80d47f787d5a
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05849736

Reaction notes

Loading…