1,2-Dichloroethane → Benzyl 3-(4-decylbenzamido)-3-(2-ethoxy-2-oxoethyl)pyrrolidine-1-carboxylate

HRID 1192908Notes

Reaction equation

HRID 1192908 reaction equation
[NH2:1][C:2]1([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1.[CH2:23]([C:33]1[CH:41]=[CH:40][C:36]([C:37](O)=[O:38])=[CH:35][CH:34]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].C(Cl)CCl.C(N(CC)CC)C>C(Cl)Cl>[CH2:23]([C:33]1[CH:34]=[CH:35][C:36]([C:37]([NH:1][C:2]2([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)=[O:8])[CH2:3]2)=[O:38])=[CH:40][CH:41]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 123614764-Decylbenzoic acidHCID 66864898Benzyl 3-amino-3-(2-ethoxy-2-oxoethyl)pyrrolidine-1-carboxylate

Product 1

HCID 66865046Benzyl 3-(4-decylbenzamido)-3-(2-ethoxy-2-oxoethyl)pyrrolidine-1-carboxylateYield 27.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of benzyl 3-amino-3-(2-ethoxy-2-oxoethyl)pyrrolidine-1-carboxylate (260 mg, 0.85 mmol) and p-decylbenzoic acid (267 mg, 1.03 mmol) in CH2Cl2 (10 mL) was added EDC (195 mg, 1.02 mmol) and triethylamine (0.35 mL, 2.55 mmol). The reaction was stirred overnight at room temperature. Methylene chloride (100 mL) was added and the solution was washed with sat. sodium bicarbonate (2×10 mL), H2O (10 mL) dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography (9:1 CH2Cl2/EtOAc) to give the title compound as a yellow solid (127 mg, 26%) 1H NMR (400 MHz, CDCl3) δ 7.64 (d, 2H, J=7.8 Hz), 7.41-7.28 (m, 5H), 7.23 (d, 2H, J=7.5 Hz), 6.40 (s, 1H), 5.21-5.10 (m, 2H), 4.10 (q, 2H, J=7.1 Hz), 4.02 (d, 1H, J=11.9 Hz), 3.64 (d, 1H, J=12.4 Hz), 3.60-3.53 (m, 2H), 3.35-2.86 (m, 2H), 2.64 (t, 2H, J=7.6 Hz), 2.14-2.02 (m, 1H), 1.67-1.56 (m, 4H), 1.36-1.24 (m, 14H), 1.21 (t, 3H, J=7.1 Hz), 0.89 (t, 3H, J=6.6 Hz).

Workup

  1. washthe solution was washed with sat. sodium bicarbonate (2×10 mL), H2O (10 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography (9:1 CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-02ddb2c690dc4ae7b0cd195fe50199b6
Source dataset
uspto-grants-2014_03
Patent number
US08680282B2

Reaction notes

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