Triethylamine → Methyl 3-(4-butyrylbenzamido)propanoate

HRID 2407016Notes

Reaction equation

HRID 2407016 reaction equation
Cl.C(N=C=NCCCN(C)C)C.[C:13]([C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=O)=[CH:20][CH:19]=1)(=[O:17])[CH2:14][CH2:15][CH3:16].Cl.[NH2:28][CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32].ON1C2N=CC=CC=2N=N1.C(N(CC)CC)C>ClCCl>[C:13]([C:18]1[CH:19]=[CH:20][C:21]([C:22]([NH:28][CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[O:24])=[CH:25][CH:26]=1)(=[O:17])[CH2:14][CH2:15][CH3:16]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 189835644-Butyrylbenzoic acid

Product 1

HCID 67981239Methyl 3-(4-butyrylbenzamido)propanoateYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-ethyl-3-(3-dimethylaminopropyl)carbodimide hydrochloride (154 mg, 0.801 mmol) was added to a solution of 4-butyrylbenzoic acid (154 mg, 0.801 mmol), methyl 3-aminopropanoate hydrochloride (90.8 mg, 0.881 mmol), 1-hydroxy-7-azabenzotriazole (109 mg, 0.801 mmol), and triethylamine (120 μL, 0.86 mmol) in dichloromethane (8.0 mL). The reaction was stirred at room temperature for 19 h. The reaction was diluted with dichloromethane and washed with water and brine. The organic layer was dried over magnesium sulfate, filtered, and concentrated. Purification by silica gel chromatography gave methyl 3-(4-butyrylbenzamido)propanoate (124.1 mg, 56%) as a colorless solid. 1H NMR (400 MHz, CDCl3) δ 7.99 (d, J=8.4 Hz, 2H), 7.83 (d, J=8.2 Hz, 2H), 6.89 (br. s., 1H), 3.69-3.77 (m, 5H), 2.95 (t, J=7.2 Hz, 2H), 2.66 (t, J=5.8 Hz, 2H), 1.71-1.82 (m, 2H), 1.00 (t, J=7.43 Hz, 3H. MS (M+1): 278.2.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-1e99dc7885f74ca8815a2894491bd803
Source dataset
uspto-grants-2014_08
Patent number
US08809342B2

Reaction notes

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