2-Propenoic acid, 3-(3-nitrophenyl)- → HCID 86758868, compound

HRID 1860333Notes

Reaction equation

HRID 1860333 reaction equation
C1C2C(COC([N:18]([C:39]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C@H:19]([C:26]([NH:28][CH2:29][CH2:30][C:31]3[CH:38]=[CH:37][C:35]([OH:36])=[C:33]([OH:34])[CH:32]=3)=[O:27])[CH2:20][CH2:21][C:22](=[O:25])[NH:23][CH3:24])=O)C3C(=CC=CC=3)C=2C=CC=1.[N+:58]([C:61]1[CH:62]=[C:63]([CH:69]=[CH:70][CH:71]=1)[CH:64]=[CH:65][C:66]([OH:68])=O)([O-:60])=[O:59]>>[N+:58]([C:61]1[CH:62]=[C:63]([CH:69]=[CH:70][CH:71]=1)[CH:64]=[CH:65][C:66]([N:18]([C:39]([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)([C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1)[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[C@H:19]([C:26]([NH:28][CH2:29][CH2:30][C:31]1[CH:38]=[CH:37][C:35]([OH:36])=[C:33]([OH:34])[CH:32]=1)=[O:27])[CH2:20][CH2:21][C:22](=[O:25])[NH:23][CH3:24])=[O:68])([O-:60])=[O:59]

Participants

3

Reactant 2

HCID 683902-Propenoic acid, 3-(3-nitrophenyl)-HCID 22976127HCID 22976127, compound

Product 1

HCID 86758868HCID 86758868, compound

Procedure

This compound was prepared from N-[Nα-(9-fluorenylmethoxycarbonyl)-Nδ-methyltrityl-L-glutaminyl]dopamine (628 mg, 0.8 mmol, example 48, step A) as described for example 48 (step B) using 3-nitrocinnamic acid (240 mg, 1.2 mmol) instead of caffeic acid. The crude material was purified by flash chromatography using successively 15%, 20% and 35% EtOAc/CH2Cl2/1% AcOH as the eluent. The title compound was obtained as a yellow powder (247 mg, 42%).

Workup

  1. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-49b6e70885d44008bcb17bf4e4ead165
Source dataset
uspto-grants-2003_03
Patent number
US06528655B1

Reaction notes

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