Tyramine → HCID 9850644, compound

HRID 2305234Notes

Reaction equation

HRID 2305234 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[CH:19]([CH2:24][C:25]4[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=4)[C:28]([OH:30])=O)[CH2:20][CH2:21][CH2:22][CH:23]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:34][CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][C:40]([OH:43])=[CH:39][CH:38]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C.CCOC(C)=O>[OH:43][C:40]1[CH:41]=[CH:42][C:37]([CH2:36][CH2:35][NH:34][C:28](=[O:30])[C:27]2[CH:31]=[CH:32][CH:33]=[C:25]([CH2:24][CH:19]3[CH2:20][CH2:21][CH2:22][CH:23]=[C:18]3[C:9]3[O:10][C:11]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)=[C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[N:8]=3)[CH:26]=2)=[CH:38][CH:39]=1

Participants

7

Reactant 4

HCID 5610TyramineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 98458443-{(2-(4,5-Diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}benzoic acid

Product 1

HCID 9850644HCID 9850644, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of (±)-3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}benzoic acid (300 mg, 0.690 mmol) and tyramine (123 mg, 0.897 mmol) in DMF (5 ml) was added 1-hydroxybenzotriazole (140 mg, 1.04 mmol) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (265 mg, 1.38mmol). After stirring the resulting mixture at room temperature for 3 hours, the reaction mixture was diluted with EtOAc (30 ml), washed with 1N-hydrochloric acid, water, saturated sodium hydrogencarbonate solution, water and brine successively, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane:EtOAc, 3:2 elution) to give (±)-N-[2-(4-hydroxyphenyl)ethyl]-3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}benzamide (358.4 mg, 94%).

Workup

  1. washwashed with 1N-hydrochloric acid, water, saturated sodium hydrogencarbonate solution, water and brine successively
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography (hexane:EtOAc, 3:2 elution)

Sources & evidence

ORD record
ord-c3d66611713c47429be33e6e830979de
Source dataset
uspto-grants-2002_08
Patent number
US06437146B1

Reaction notes

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