Caffeic Acid → HCID 9910538, compound

HRID 278849

Reaction equation

HRID 278849 reaction equation
C(O[C:9]([NH:11][C@H:12]([C:21]([NH:23][CH2:24][CH2:25][C:26]1[CH:33]=[CH:32][C:30]([OH:31])=[C:28]([OH:29])[CH:27]=1)=[O:22])[CH2:13][C:14](=[O:20])[O:15]C(C)(C)C)=[O:10])C1C=CC=CC=1.C(O)(=O)/[CH:35]=[CH:36]/[C:37]1[CH:44]=[CH:43][C:41]([OH:42])=[C:39]([OH:40])[CH:38]=1>>[C:9]([NH:11][C@H:12]([C:21]([NH:23][CH2:24][CH2:25][C:26]1[CH:33]=[CH:32][C:30]([OH:31])=[C:28]([OH:29])[CH:27]=1)=[O:22])[CH2:13][C:14](=[O:20])[OH:15])(=[O:10])/[CH:35]=[CH:36]/[C:37]1[CH:44]=[CH:43][C:41]([OH:42])=[C:39]([OH:40])[CH:38]=1

Participants

3

Reactant 2

HCID 689043Caffeic AcidHCID 131723152HCID 131723152, compound

Product 1

HCID 9910538HCID 9910538, compoundYield 52.4%

Procedure

N-(N′-benzyloxycarbonyl-Oγ-tert-butyl-L-aspartyl)dopamine (1.0 g, 2.3 mmol) was deprotected by hydrogenolysis as described in example 5. The product thus obtained was then coupled with caffeic acid (621 mg, 3.5 mmol) according to the indications of example 4. Purification by flash chromatography using 30-50% AcOEt/CH2Cl2 containing 1% AcOH yielded 519 mg (47%) of the title compound as yellow crystals.

Workup

  1. customThe product thus obtained
  2. customPurification by flash chromatography

Sources & evidence

ORD record
ord-255f868c04ff4cfaadfd676d1d709f94
Source dataset
uspto-grants-2002_03
Patent number
US06362165B1

Linked notes

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