Triethylamine → Methyl 3-(4-butyrylbenzamido)propanoate

HRID 2173878Notes

Reaction equation

HRID 2173878 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)carbodiimide 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-a145fd914e70464190a6add3441cda43
Source dataset
uspto-grants-2015_06
Patent number
US09056834B2

Reaction notes

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