Caffeic Acid → N-[(1S)-1-(tert-butoxymethyl)-2-[2-(3,4-dihydroxyphenyl)ethylamino]-2-oxo-ethyl]-3,4-bis[(4-fluorophenyl)methoxy]benzamide

HRID 1860344Notes

Reaction equation

HRID 1860344 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.[F:39][C:40]1[CH:65]=[CH:64][C:43]([CH2:44][O:45][C:46]2[CH:47]=[C:48]([CH:52]=[CH:53][C:54]=2[O:55][CH2:56][C:57]2[CH:62]=[CH:61][C:60]([F:63])=[CH:59][CH:58]=2)C(O)=O)=[CH:42][CH:41]=1.C(O)(=O)/C=C/C1C=CC(O)=C(O)C=1>>[F:39][C:40]1[CH:41]=[CH:42][C:43]([CH2:44][O:45][C:46]2[CH:47]=[C:48]([CH:52]=[CH:53][C:54]=2[O:55][CH2:56][C:57]2[CH:58]=[CH:59][C:60]([F:63])=[CH:61][CH:62]=2)[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:64][CH:65]=1

Participants

4

Reactant 3

HCID 689043Caffeic AcidHCID 186270553,4-Di-(4-fluorobenzyloxy)benzoic acidHCID 22976135N-[Nalpha-(9-fluorenylmethoxycarbonyl)-O-tert-butyl-L-seryl]dopamine

Product 1

HCID 504861N-[(1S)-1-(tert-butoxymethyl)-2-[2-(3,4-dihydroxyphenyl)ethylamino]-2-oxo-ethyl]-3,4-bis[(4-fluorophenyl)methoxy]benzamide

Procedure

The title compound was prepared from N-[Nα-(9-fluorenylmethoxycarbonyl)-O-tert-butyl-L-seryl]dopamine (610 mg, 1.2 mmol, example 42, step A) as described for example 42 (step B) using 3,4-di-(4-fluorobenzyloxy)benzoic acid (653 mg, 1.8 mmol, step A of this example) instead of caffeic acid. The crude material was purified by flash chromatography using successively 15%, 35% and 50% EtOAc/CH2Cl2 as the eluent. The title compound was obtained as a yellow powder (207 mg, 27%).

Workup

  1. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-4720430f4c6e4fdea395d172c47c2bcf
Source dataset
uspto-grants-2003_03
Patent number
US06528655B1

Reaction notes

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