5729-47-5 → HCID 59445878, compound

HRID 1886849Notes

Reaction equation

HRID 1886849 reaction equation
[O:1]=[C:2]([CH3:7])/[CH:3]=[CH:4]/[CH:5]=[O:6].[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([N:19]=[CH:20]/[CH:21]=[CH:22]/[CH2:23][CH2:24][CH3:25])(=[O:18])=[O:17])=[CH:12][CH:11]=1>C(Cl)(Cl)Cl>[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([S:16]([N:19]2[CH:20]=[CH:21][C@H:22]([CH2:23][CH2:24][CH3:25])[C@H:4]([CH2:3][C:2](=[O:1])[CH3:7])[C:5]2=[O:6])(=[O:18])=[O:17])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 64334475729-47-5HCID 68486321HCID 68486321, compound

Product 1

HCID 59445878HCID 59445878, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The title compound was prepared according to the general procedure from (E)-4-oxopent-2-enal and trans-N-(4-methoxybenzenesulfonyl)-hex-2-en-1-imine using 10 mol % 9 as the catalyst in 70% yield as a yellow oil. [α]D20 (c 0.91, CHCl3)=−5.7; 1H NMR (400 MHz, CDCl3) δ 7.91 (dd, 2H, J=6.9, 2.0 Hz), 6.97 (dd, 2H, J=6.9, 2.0 Hz), 5.54 (dd, 1H, J=8.0, 6.6 Hz), 3.87 (s, 3H), 3.24 (q, 1H, J=6.3 Hz), 2.82 (dd, 1H, J=16.6, 7.2 Hz), 2.41-2.38 (m, 1H), 2.24 (dd, 1H, J=16.6, 7.0 Hz), 1.22 (t, 3H, J=7.2 Hz), 1.25-1.02 (m, 4H), 0.73 (t, 3H, J=7.2 Hz); 13C NMR (100 MHz, CDCl3) δ 206.0, 170.7, 164.1, 131.0, 129.6, 128.8, 124.1, 115.1, 114.4, 114.1, 55.9, 42.4, 39.8, 34.7, 32.1, 30.6, 19.5, 14.3; IR (thin film) ν 3010, 2957, 1713, 1595, 1497, 1362, 1262, 1092, 1023 cm−1; HRMS (ESI) calcd for C18H23NO5S [M+Na]+ 388.1189, found 388.1175; 98% ee (3S,4S)-isomer as determined by HPLC (AS-H, 9:1 hexanes/i-PrOH), tr (3S,4S)=68.1 min, tr (3R,4R)=55.1 min.

Sources & evidence

ORD record
ord-243b914d0f554e9d9227a767e94a8163
Source dataset
uspto-grants-2013_08
Patent number
US08501658B2

Reaction notes

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