Caffeic Acid → HCID 18711615, compound

HRID 278850

Reaction equation

C(O[C:6]([NH:8][C@H:9]([C:18]([NH:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([OH:29])[CH:23]=1)=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)=[O:7])(C)(C)C.C(O)(=O)/[CH:31]=[CH:32]/[C:33]1[CH:40]=[CH:39][C:37]([OH:38])=[C:35]([OH:36])[CH:34]=1>>[C:6]([NH:8][C@H:9]([C:18]([NH:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([OH:29])[CH:23]=1)=[O:19])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1)(=[O:7])/[CH:31]=[CH:32]/[C:33]1[CH:40]=[CH:39][C:37]([OH:38])=[C:35]([OH:36])[CH:34]=1

Participants

Reactant 2

HCID 689043Caffeic Acid

HCID 18711627HCID 18711627, compound

Product 1

HCID 18711615HCID 18711615, compoundYield 51.2%

Procedure

The title compound was prepared from N-(N-tert-butoxycarbonyl-L-tyrosyl)-3,4-dihydroxybenzylamine (example 56, step A) (1.4 g, 3.3 mmol) according to the indications of example 3, for 2 h. The crude intermediate was coupled with caffeic acid (978 mg, 5.4 mmol) according to the indications of example 4. The crude product was purified by flash chromatography using 40-80% AcOEt/CH2Cl2 containing 1% AcOH to yield the title product as yellow crystals (784 mg, 47%).

Workup

customThe crude product was purified by flash chromatography

Sources & evidence

ORD record: ord-57506a0334f94bb791230b8a5230b180
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06362165B1

Linked notes

Loading…