N-[Nalpha-(9-fluorenylmethoxycarbonyl)-Ngamma-trityl-L-asparagyl]dopamine → HCID 178520774, compound

HRID 1860336Notes

Reaction equation

HRID 1860336 reaction equation
C1C2C(CO[C:16]([NH:18][C@H:19]([C:43]([NH:45][CH2:46][CH2:47][C:48]3[CH:55]=[CH:54][C:52]([OH:53])=[C:50]([OH:51])[CH:49]=3)=[O:44])[CH2:20][C:21](=[O:42])[NH:22][C:23]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:17])C3C(=CC=CC=3)C=2C=CC=1.[OH:56][C:57]1[C:66]2[C:61](=[C:62]([OH:67])[CH:63]=[CH:64][CH:65]=2)[N:60]=[C:59](C(O)=O)[CH:58]=1>>[OH:56][C:57]1[C:66]2[C:61](=[C:62]([OH:67])[CH:63]=[CH:64][CH:65]=2)[N:60]=[C:59]([C:16]([NH:18][C@H:19]([C:43]([NH:45][CH2:46][CH2:47][C:48]2[CH:55]=[CH:54][C:52]([OH:53])=[C:50]([OH:51])[CH:49]=2)=[O:44])[CH2:20][C:21](=[O:42])[NH:22][C:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:17])[CH:58]=1

Participants

3

Reactant 2

HCID 22976130N-[Nalpha-(9-fluorenylmethoxycarbonyl)-Ngamma-trityl-L-asparagyl]dopamineHCID 1785245884,8-dihydroxyquinoline-2-carboxylic acid

Product 1

HCID 178520774HCID 178520774, compound

Procedure

The title compound was prepared from N-[Nα-(9-fluorenylmethoxycarbonyl)-Nγ-trityl-L-asparagyl]dopamine (1.34 g, 1.8 mmol, example 7, step A) as described for example 7 (step B) using 4,8-dihydroxyquinoline-2-carboxylic acid (564 mg, 2.75 mmol) instead of caffeic acid. The crude material was purified by flash chromatography using a solvent gradient from 30% to 60% EtOAc/CH2Cl2 containing 1% AcOH. The title compound was obtained as yellow crystals (663 mg, 52%).

Workup

  1. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-c5cdea4cbce54859b665f94441b565c1
Source dataset
uspto-grants-2003_03
Patent number
US06528655B1

Reaction notes

Loading…