Ethyl (2E)-4-oxo-2-butenoate → Ethyl 2-((3S,4S)-4-(4-methoxyphenyl)-1-(4-methoxyphenylsulfonyl)-2-oxo-1,2,3,4-tetra-hydropyridin-3-yl)acetate

HRID 1886845Notes

Reaction equation

HRID 1886845 reaction equation
[O:1]=[CH:2]/[CH:3]=[CH:4]/[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([N:21]=[CH:22]/[CH:23]=[CH:24]/[C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)(=[O:20])=[O:19])=[CH:14][CH:13]=1>C(Cl)(Cl)Cl>[CH3:32][O:31][C:28]1[CH:29]=[CH:30][C:25]([C@H:24]2[CH:23]=[CH:22][N:21]([S:18]([C:15]3[CH:14]=[CH:13][C:12]([O:11][CH3:10])=[CH:17][CH:16]=3)(=[O:20])=[O:19])[C:2](=[O:1])[C@H:3]2[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 7019541Ethyl (2E)-4-oxo-2-butenoateHCID 68484489trans-N-(4-methoxybenzenesulfonyl)-3-(4-methoxyphenyl)prop-2-en-1-imine

Product 1

HCID 59445882Ethyl 2-((3S,4S)-4-(4-methoxyphenyl)-1-(4-methoxyphenylsulfonyl)-2-oxo-1,2,3,4-tetra-hydropyridin-3-yl)acetateYield 81%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The title compound was prepared according to the general procedure from ethyl trans-4-oxo-2-butenoate and trans-N-(4-methoxybenzenesulfonyl)-3-(4-methoxyphenyl)prop-2-en-1-imine using 10 mol % 9 as the catalyst in 81% yield as a yellow solid. [α]D20 (c 1.04, CHCl3)=+143.6; mp=107-110° C.; 1H NMR (400 MHz, CDCl3) δ 8.03 (dd, 2H, J=7.1, 1.8 Hz), 7.13 (d, 1H, J=8.1 Hz), 7.05 (dd, 2H, J=7.1, 1.8 Hz), 6.55-6.48 (m, 4H), 5.59 (dd, 1H, J=8.0, 6.6 Hz), 4.16-4.09 (m, 2H), 3.92 (s, 3H), 3.71 (s, 3H), 3.60 (t, 1H, J=6.9 Hz), 3.52-3.47 (m, 1H), 2.58 (dd, 1H, J=17.2, 6.0 Hz), 1.95 (dd, 1H, J=17.2, 7.7 Hz), 1.22 (t, 3H, J=7.0 Hz); 13C NMR (100 MHz, CDCl3) δ 171.8, 169.1, 164.3, 159.2, 131.4, 129.2, 128.5, 124.3, 114.3, 114.3, 113.9, 113.6, 61.0, 56.0, 55.3, 44.3, 41.2, 31.5, 14.4; IR (thin film) ν 3055, 2840, 1720, 1647, 1511, 1498, 1463, 1442, 1366, 1263, 1167, 1090, 1028 cm−1; HRMS (ESI) calcd for C23H25NO7S [M+Na]+ 482.1243, found 482.1253; >99% ee (3S,4S)-isomer as determined by HPLC (AS-H, 4:1 hexanes/i-PrOH), tr (3S,4S)=49.3 min, tr (3R,4R)=29.6 min.

Sources & evidence

ORD record
ord-cbf4fdb1ae8640e6944639b2f9281e0c
Source dataset
uspto-grants-2013_08
Patent number
US08501658B2

Reaction notes

Loading…