Triethylamine → HCID 67795255, compound

HRID 1034233Notes

Reaction equation

HRID 1034233 reaction equation
[NH2:1][CH:2]1[C:6](=[O:7])[N:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:4][CH:3]1[C:13]([O:15][CH2:16][CH3:17])=[O:14].C(N(CC)CC)C.[CH:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][C:26]=1[C:35](Cl)=[O:36]>C(Cl)Cl>[CH:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][C:26]=1[C:35]([NH:1][C@H:2]1[C:6](=[O:7])[N:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:4][C@H:3]1[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 752462-Naphthoyl chlorideHCID 19023543HCID 19023543, compound

Product 1

HCID 67795255HCID 67795255, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the aminopyrrolidinone of Example R (120 mg, 0.495 mmol) and triethylamine (0.35 ml, 2.48 mmol) in CH2Cl2 was added a solution of 2-naphthoyl chloride (94 mg, 0.495 mmol) in CH2Cl2 dropwise via syringe. After stirring for 12 h at room temperature the reaction mixture was evaporated in vacuo to give a residue which was chromatographed on silica gel eluting with EtOH/CH2Cl2 (2%-5%) to give the title compound (172 mg, 69%) as a colorless solid. MS M+1 calcd for C23H28N2O4 397; found 397.

Workup

  1. customwas evaporated in vacuo
  2. customto give a residue which
  3. customwas chromatographed on silica gel eluting with EtOH/CH2Cl2 (2%-5%)

Sources & evidence

ORD record
ord-d4ff979fa8dd451890ab73bcb99d41ac
Source dataset
uspto-grants-1994_05
Patent number
US05314886

Reaction notes

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