Alpha-Cyano-4-Hydroxycinnamic Acid → HCID 178489567, compound

HRID 1977970Notes

Reaction equation

C(OC([N:8]([O:19][CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:29]=[C:28]([CH3:30])[CH:27]=[C:26]([O:31][S:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[S:41]([N:44]2[CH2:49][CH2:48][N:47]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=3[O:56][CH3:57])[CH2:46][CH2:45]2)(=[O:43])=[O:42])(=[O:34])=[O:33])[CH:25]=1)[C:9]([NH:11]C(OC(C)(C)C)=O)=[NH:10])=O)(C)(C)C.[ClH:58].CO.C(C(=CC1C=CC(O)=CC=1)C(O)=O)#N>>[ClH:58].[CH3:30][C:28]1[CH:27]=[C:26]([O:31][S:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[S:41]([N:44]2[CH2:45][CH2:46][N:47]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=3[O:56][CH3:57])[CH2:48][CH2:49]2)(=[O:42])=[O:43])(=[O:33])=[O:34])[CH:25]=[C:24]([CH:29]=1)[O:23][CH2:22][CH2:21][CH2:20][O:19][NH:8][C:9]([NH2:11])=[NH:10]

Participants

Reactant 3

HCID 2102Alpha-Cyano-4-Hydroxycinnamic Acid

HCID 21893726Hydrochloride methanol

HCID 139887074HCID 139887074, compound

Product 1

HCID 178489567HCID 178489567, compoundYield 33%

Procedure

The title compound was prepared in 33% yield from N,N′-bis-(tert-butoxycarbony)-3-[5-methyl-3-(2-(4-(2-methoxyphenyl)piperazinylsulfonyl)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) δ8.21 (m, 2H), 7.81 (t, 1H, J=7.5 Hz), 7.69 (t, 1H, J=7.5 Hz), 7.00 (m, 1H), 6.89 (m, 3H), 6.58 (s, 2H), 6.53 (s, 1H), 3.95 (m, 4H), 3.82 (s, 3H), 3.53 (m, 4H), 3.11 (m, 4H), 2.22 (s, 3H), 2.03 (m, 2H). Mass spectrum (MALDI-TOF, α-cyano-4-hydroxycinnamic acid matrix) calcd. for C28H35N5O8S2: 634.2 (M+H), 656.2 (M+Na). Found: 634.2, 656.3.

Sources & evidence

ORD record: ord-f4e50bf8407d4faf950112e3dc3c968e
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06235778B1

Reaction notes

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