(Ethylsulfonyl)ethene → HCID 58617364, compound

HRID 2223144Notes

Reaction equation

[CH2:1]([S:3]([CH2:6][CH2:7][N:8]([C@@H:23]([C:25]1[N:26]([C:36]2[CH:41]=[CH:40][C:39]([O:42][CH2:43][C:44]([F:47])([F:46])[F:45])=[CH:38][CH:37]=2)[C:27](=[O:35])[C:28]2[CH:34]=[CH:33][CH:32]=[N:31][C:29]=2[N:30]=1)[CH3:24])[C:9](=[O:22])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:12]=1)(=[O:5])=[O:4])C.C(S(CC)(=O)=O)=C>>[F:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][C:9]([N:8]([CH2:7][CH2:6][S:3]([CH3:1])(=[O:4])=[O:5])[C@@H:23]([C:25]2[N:26]([C:36]3[CH:37]=[CH:38][C:39]([O:42][CH2:43][C:44]([F:47])([F:46])[F:45])=[CH:40][CH:41]=3)[C:27](=[O:35])[C:28]3[CH:34]=[CH:33][CH:32]=[N:31][C:29]=3[N:30]=2)[CH3:24])=[O:22])=[CH:12][C:13]=1[C:18]([F:21])([F:19])[F:20]

Participants

Reactant 2

HCID 74680(Ethylsulfonyl)ethene

HCID 45101529HCID 45101529, compound

Product 1

HCID 58617364HCID 58617364, compound

Procedure

Compound B2 was synthesized in two steps from A1 following the previously described synthetic sequence for A3, substituting methyl vinyl sulfone for ethyl vinyl sulfone in the first step. 1H NMR: a mixture of cis/trans amide rotamers in ca. 2.0:1 ratio (400 MHz; CDCl3; T=298 K) δmajor 8.98 (dd, J=4.46, 1.78 Hz, 1H), 8.62 (dd, 7.69, 1.78 Hz, 1H), 7.66 (dd, J=9.71, 3.33 Hz, 1H), 7.10-7.46 (m, 7H), 5.14 (q, J=7.26 Hz, 1H), 4.41 (q, J=7.94 Hz, 2H), 3.64-4.24 (m, 5H), 3.10 (s, 3H), 2.47 (m, 1H), 1.46 (d, J=7.2 Hz, 3H) and δminor 9.06 (m, 1H), 8.63 (obscured dd, J=7.28, 1.63 Hz, 1H), 5.01 (q, J=6.64 Hz, 1H), 2.83 (s, 3H), 1.58 (d, J=6.71 Hz, 3H) ppm. MS (ESI+) 675 [M+H]+.

Sources & evidence

ORD record: ord-4e713b97a0a2475d8424f049abb6c020
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07375102B2

Reaction notes

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