N-[Nalpha-(9-fluorenylmethoxycarbonyl)-O-tert-butyl-L-seryl]dopamine → HCID 178450475, compound

HRID 1860338Notes

Reaction equation

HRID 1860338 reaction equation
C1C2C(CO[C:16]([NH:18][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][O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:17])C3C(=CC=CC=3)C=2C=CC=1.[OH:39][C:40]1[C:49]2[C:44](=[C:45]([OH:50])[CH:46]=[CH:47][CH:48]=2)[N:43]=[C:42](C(O)=O)[CH:41]=1>>[OH:39][C:40]1[C:49]2[C:44](=[C:45]([OH:50])[CH:46]=[CH:47][CH:48]=2)[N:43]=[C:42]([C:16]([NH:18][C@H:19]([C:26]([NH:28][CH2:29][CH2:30][C:31]2[CH:38]=[CH:37][C:35]([OH:36])=[C:33]([OH:34])[CH:32]=2)=[O:27])[CH2:20][O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:17])[CH:41]=1

Participants

3

Reactant 2

HCID 22976135N-[Nalpha-(9-fluorenylmethoxycarbonyl)-O-tert-butyl-L-seryl]dopamineHCID 1785245884,8-dihydroxyquinoline-2-carboxylic acid

Product 1

HCID 178450475HCID 178450475, compound

Procedure

The title compound was prepared from N-[Nα-(9-fluorenylmethoxycarbonyl)-O-tert-butyl-L-seryl]dopamine (676 mg, 1.3 mmol, example 42, step A) as described for example 42 (step B) using 4,8-dihydroxyquinoline-2-carboxylic acid (402 mg, 1.96 mmol) instead of caffeic acid. The crude material was purified by flash chromatography using successively 30%, 40% and 70% EtOAc/CH2Cl2/1% AcOH as the eluent. The title compound was obtained as a yellow powder (130 mg, 21%).

Workup

  1. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-29d5de7b29f945e0867d009833e968a2
Source dataset
uspto-grants-2003_03
Patent number
US06528655B1

Reaction notes

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