Alpha-Cyano-4-Hydroxycinnamic Acid → HCID 178429056, compound
Reaction equation
C(ONC(N)=N)CC.C(OC([N:16]([O:27][CH2:28][CH2:29][CH2:30][O:31][C:32]1[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([O:39][S:40]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=2[S:49]([N:52]([CH2:59][CH2:60][C:61]#[N:62])[CH2:53][C:54]2[O:55][CH:56]=[CH:57][CH:58]=2)(=[O:51])=[O:50])(=[O:42])=[O:41])[CH:33]=1)[C:17]([NH:19]C(OC(C)(C)C)=O)=[NH:18])=O)(C)(C)C.Cl.CO.C(C(=CC1C=CC(O)=CC=1)C(O)=O)#N>>[CH3:38][C:36]1[CH:35]=[C:34]([O:39][S:40]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=2[S:49]([N:52]([CH2:59][CH2:60][C:61]#[N:62])[CH2:53][C:54]2[O:55][CH:56]=[CH:57][CH:58]=2)(=[O:50])=[O:51])(=[O:41])=[O:42])[CH:33]=[C:32]([CH:37]=1)[O:31][CH2:30][CH2:29][CH2:28][O:27][NH:16][C:17]([NH2:19])=[NH:18]Participants
Procedure
3-5-methyl-3-(2-(N-(2-cyanoethyl)-N-(2-furanylmethyl)aminosulfonyl)phenylsulfonyloxy)phenoxy]propoxyguanidine: The title compound was prepared in 42% yield from N,N′-bis-(tert-butoxycarbony)-3-[5-methyl-3-(2-(N-(2-cyanoethyl)-N-(2-furanylmethyl)aminosulfonyl)phenylsulfonyloxy)phenoxy]propoxyguanidine, as prepared in the previous step, in a manner analogous to step i of Example 20 (without HCl-methanol acidification). 1H NMR (300 MHz, CDCl3) δ 8.23 (dd, 1H, J=7.9, 1.3 Hz), 8.14 (dd, 1H, J=7.9, 1.4 Hz), 7.76 (td, 1H, J=7.7, 1.4 Hz), 7.67 (td, 1H, J=7.7, 1.3 Hz), 7.29 (t, 1H, J=1.3 Hz), 6.56 (m, 2H), 6.51 (m, 1H), 6.28 (m, 2H), 4.61 (s, 2H), 3.91 (m, 4H), 3.62 (t, 2H, J=7.1 Hz), 2.53 (t, 2H, J=7.1 Hz), 2.20 (s, 3H), 2.00 (pentet, 2H, J=6.1 Hz). Mass spectrum (MALDI-TOF, α-cyano-4-hydroxycinnamic acid matrix) calcd. for C25H29N5O8S2: 592.2 (M+H), 614.1 (M+Na). Found: 592.2, 614.4.
Sources & evidence
- ORD record
- ord-50919158208e45f1a81d5862dc9b48ce
- Source dataset
- uspto-grants-2004_05
- Patent number
- US06730783B2
Reaction notes
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