Guaiacylacetone → HCID 86758081, compound

HRID 1936742Notes

Reaction equation

HRID 1936742 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=O)[CH3:10])=[CH:4][C:3]=1[O:12][CH3:13].Br[CH2:15][CH2:16][CH:17]([NH:23][C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])[C:18]([O:20]CC)=[O:19].Br.[NH:35]1[CH2:39][CH2:38][N:37]=[C:36]1[NH:40][NH2:41]>CO>[NH:37]1[CH2:38][CH2:39][N:35]=[C:36]1[NH:40][N:41]=[C:9]([CH3:10])[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([O:1][CH2:15][CH2:16][C@@H:17]([C:18]([OH:20])=[O:19])[NH:23][C:24]([O:26][CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[O:25])=[C:3]([O:12][CH3:13])[CH:4]=1

Participants

5

Reactant 3

HCID 17262GuaiacylacetoneHCID 30850992-Hydrazino-delta-2-imidazoline hydrobromideHCID 15857342HCID 15857342, compound

Product 1

HCID 86758081HCID 86758081, compoundYield 0.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The operation is carried out as in Example 1 Stages A, B and C but using 900 mg of 3-(4-hydroxy-3-methoxyphenyl)-2-propanone and 1.80 g of ethyl 4-bromo-2-[[(phenylmethoxy)carbonyl]amino]butanoate (Stage A) then, during Stage B, 1.47 g of 4,5-dihydro-1H-imidazol-2-yl-hydrazine hydrobromide. The saponificaton stage is carried out in the presence of soda in methanol. 20 mg of expected product is obtained in the form of an E/7 mixture 90/10

Sources & evidence

ORD record
ord-3342d9d747044377846e379a2c301161
Source dataset
uspto-grants-2002_05
Patent number
US06391904B1

Reaction notes

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