Dopamine Hydrochloride → (2S)-N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]amino]-N'-trityl-butanediamide

HRID 1860321Notes

Reaction equation

C1C2C(C[O:15][C:16]([NH:18][C@H:19]([C:43]([OH:45])=O)[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)C3C(=CC=CC=3)C=2C=CC=1.Cl.[NH2:47][CH2:48][CH2:49][C:50]1[CH:57]=[CH:56][C:54]([OH:55])=[C:52]([OH:53])[CH:51]=1>>[C:16]([NH:18][C@H:19]([C:43]([NH:47][CH2:48][CH2:49][C:50]1[CH:57]=[CH:56][C:54]([OH:55])=[C:52]([OH:53])[CH:51]=1)=[O:45])[CH2:20][C:21](=[O:42])[NH:22][C:23]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)(=[O:15])/[CH:48]=[CH:49]/[C:50]1[CH:57]=[CH:56][C:54]([OH:55])=[C:52]([OH:53])[CH:51]=1

Participants

Reactant 2

HCID 65340Dopamine Hydrochloride

HCID 640248Fmoc-Asn(Trt)-OH

Product 1

HCID 6478497(2S)-N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]amino]-N'-trityl-butanediamideYield 137%

Procedure

The title compound was prepared from Nα-(9-fluorenylmethoxycarbonyl)-Nγ-trityl-L-asparagine (2.0 g, 3.4 mmol) following the indications of general procedure F with dopamine hydrochloride (954 mg, 5 mmol). The crude material was purified by flash chromatography with a solvent gradient from 15% to 60% EtOAc/CH2Cl2 to give 2.3 g (95%) of the desired product as white crystals.

Workup

customThe crude material was purified by flash chromatography with a solvent gradient from 15% to 60% EtOAc/CH2Cl2

Sources & evidence

ORD record: ord-260253ffdada467283e73aa01b48066e
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06528655B1

Reaction notes

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