Sodium Chloride → {Phenethyl-(5-(3-propyl)-1H-imidazole-2-carbonyl)amino}acetic acid tert-butyl ester

HRID 2229933Notes

Reaction equation

HRID 2229933 reaction equation
C1([CH2:7][CH2:8][CH2:9][C:10]2[N:11]=[C:12]([C:15]([OH:17])=O)[NH:13][CH:14]=2)C=CC=CC=1.[CH:18]([N:21](C(C)C)CC)(C)[CH3:19].O[C:28]1[C:36]2N=NN[C:32]=2[CH:31]=[CH:30][CH:29]=1.Cl.[CH3:38]N(C)CCCN=C=NCC.[Cl-].[Na+].[C:51]([O:54]CC)(=[O:53])[CH3:52].CCC[CH2:60][CH2:61][CH3:62]>CN(C)C=O>[C:61]([O:54][C:51](=[O:53])[CH2:52][N:21]([CH2:18][CH2:19][C:28]1[CH:36]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:15]([C:12]1[NH:11][C:10]([CH2:9][CH2:8][CH3:7])=[CH:14][N:13]=1)=[O:17])([CH3:60])([CH3:62])[CH3:38]

Participants

8

Reactant 6

HCID 5234Sodium ChlorideHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21226206Ethyl acetate hexaneHCID 178418300HCID 178418300, compoundHCID 178524887HCID 178524887, compound

Product 1

HCID 54027469{Phenethyl-(5-(3-propyl)-1H-imidazole-2-carbonyl)amino}acetic acid tert-butyl esterYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 0° C. solution of 4-(3-phenylpropyl)-imidazole-2-carboxylic (13d) (150 mg, 0.65 mmol) and N-(2-phenethyl)glycine tert-butyl ester (140 mg, 0.59 mmol) in 5 ml of anhydrous dimethylformamide was treated with diisopropylethylamine (154 μl, 0.89 mmol), hydroxybenzotriazole (160 mg, 1.18 mmol), and 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (136 mg, 0.71 mmol). After stirring for 36 h, the reaction was poured onto saturated aqueous sodium chloride and extracted with ethyl acetate (3×50 ml) The combined organic extracts were washed twice with saturated aqueous sodium bicarbonate (2×) and saturated aqueous sodium chloride (1×), dried (Na2SO4), filtered, and concentrated in vacuo to give a brown oil. Chromatography (flash, SiO2, 30% ethyl acetate/hexane) to give 160 mg (61%) of 23 as a white solid: 1H NMR (CDCl3) δ7.38-7.14 (10H, m), 6.85-6.8 (1H, m), 4.84-4.76 (1H, d), 4.5-4.42 (1H, m), 4.07-4.0 (1H, d), 3.78-3.72 (1H, m), 3.12-2.94 (2H, 2×m), 2.75-2.55 (4H, m), 2.1-1.95 (2H,m), 1.5-1.45 (9H, 3×s).

Workup

  1. extractionextracted with ethyl acetate (3×50 ml) The combined organic extracts
  2. washwere washed twice with saturated aqueous sodium bicarbonate (2×) and saturated aqueous sodium chloride (1×)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a brown oil

Sources & evidence

ORD record
ord-d7c9d61fc1084ff19ccea3c8533cbdf8
Source dataset
uspto-grants-2002_07
Patent number
US06420522B1

Reaction notes

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