Triethylamine → (9H-fluoren-9-yl)methyl 2-(5-bromo-2-carbamoylphenylcarbamoyl)pyrrolidine-1-carboxylate

HRID 1619343Notes

Reaction equation

HRID 1619343 reaction equation
Cl[C:2]([CH:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([O:11][CH2:12][CH:13]1[C:25]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:19]2[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])=[O:3].[NH2:26][C:27]1[CH:35]=[C:34]([Br:36])[CH:33]=[CH:32][C:28]=1[C:29]([NH2:31])=[O:30].CCN(CC)CC>C1COCC1.O>[Br:36][C:34]1[CH:33]=[CH:32][C:28]([C:29](=[O:30])[NH2:31])=[C:27]([NH:26][C:2]([CH:4]2[CH2:8][CH2:7][CH2:6][N:5]2[C:9]([O:11][CH2:12][CH:13]2[C:25]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:19]3[C:14]2=[CH:15][CH:16]=[CH:17][CH:18]=3)=[O:10])=[O:3])[CH:35]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 138055072-Amino-4-bromobenzamideHCID 14482361(9H-fluoren-9-yl)methyl 2-(chlorocarbonyl)pyrrolidine-1-carboxylate

Product 1

HCID 58574511(9H-fluoren-9-yl)methyl 2-(5-bromo-2-carbamoylphenylcarbamoyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (9H-fluoren-9-yl)methyl 2-(chlorocarbonyl)pyrrolidine-1-carboxylate (600 mg, 1.8 mmol), 2-amino-4-bromobenzamide (400 mg, 1.8 mmol), and Et3N (2 mL) in THF was stirred at room temperature. The reaction was monitored by TLC. After diluting with H2O (50 mL), the mixture was extracted with ethyl acetate (3×100 mL). The organic layers were dried over Na2SO4 and concentrated to give yellow residue, which was purified by column chromatography. MS (ESI): 534, 536 (MH+)

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×100 mL)
  2. dry with materialThe organic layers were dried over Na2SO4
  3. concentrationconcentrated
  4. customto give yellow residue, which
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-80ab98acd119418d8e94d5b5d8e22f06
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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