Caffeic Acid → HCID 6480426, compound

HRID 1860339Notes

Reaction equation

HRID 1860339 reaction equation
OC1C2C(=C(O)C=CC=2)N=C(C([NH:15][C@H:16]([C:25]([NH:27][NH:28][C:29](=[O:37])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[OH:36])=[O:26])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)=O)C=1.[C:38]([OH:50])(=O)/[CH:39]=[CH:40]/[C:41]1[CH:48]=[CH:47][C:45]([OH:46])=[C:43]([OH:44])[CH:42]=1>>[C:38]([NH:15][C@H:16]([C:25]([NH:27][NH:28][C:29](=[O:37])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[OH:36])=[O:26])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1)(=[O:50])/[CH:39]=[CH:40]/[C:41]1[CH:48]=[CH:47][C:45]([OH:46])=[C:43]([OH:44])[CH:42]=1

Participants

3

Reactant 2

HCID 689043Caffeic AcidHCID 178523859HCID 178523859, compound

Product 1

HCID 6480426HCID 6480426, compoundYield 25%

Procedure

N1-[Nα-(tert-butoxycarbonyl)-L-tyrosyl]-N2-(2-hydroxybenzoyl)-hydrazine (349 mg, 0.84 mmol) prepared in example 73, step A was deprotected following the indications of general procedure C and coupled with caffeic acid (230 mg, 1.3 mmol) using general procedure D. The final product was purified by flash chromatography eluting with 40% EtOAc/CH2Cl2 then successively 5% and 10% MeOH/CH2Cl2 to yield 100 mg, 25% of the title compound.

Workup

  1. customThe final product was purified by flash chromatography
  2. washeluting with 40% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-8b49f6458d5b46c09d71b2687d9524ac
Source dataset
uspto-grants-2003_03
Patent number
US06528655B1

Reaction notes

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