Tyramine → HCID 58603734, compound

HRID 14961Notes

Reaction equation

C(OC([N:8]1[CH2:14][CH2:13][S:12](=[O:16])(=[O:15])[N:11]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]3[CH:29]=[CH:28][N:27]=[C:26](Cl)[N:25]=3)[CH:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[NH2:31][CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][CH:35]=1>>[O:15]=[S:12]1(=[O:16])[CH2:13][CH2:14][NH:8][CH2:9][CH2:10][N:11]1[CH2:17][C:18]1[CH:19]=[C:20]([C:24]2[CH:29]=[CH:28][N:27]=[C:26]([NH:31][CH2:32][CH2:33][C:34]3[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][CH:35]=3)[N:25]=2)[CH:21]=[CH:22][CH:23]=1

Participants

Reactant 2

HCID 5610Tyramine

HCID 86603327HCID 86603327, compound

Product 1

HCID 58603734HCID 58603734, compound

Procedure

Intermediate 144 was coupled with tyramine following procedure F. The resulting product was deprotected following procedure G2. LC-MS showed the product had the expected M+H+ of 454. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.36 (s, 1H) 8.30 (d, 1H) 8.20 (d, 1H) 7.73 (d, 1H) 7.64 (t 1H) 7.53 (d, 1H) 7.14 (d, 2H) 6.68 (d, 2H) 4.70 (s, 2H) 3.80 (t, 2H) 3.67 (m, 4H) 3.56 (t, 2H) 3.36 (t, 2H) 2.95 (t, 2H).

Sources & evidence

ORD record: ord-fc40b7240dbe4fcdb9f863ce894667bf
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732444B2

Reaction notes

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