Triethylamine → HCID 59350824, compound

HRID 1644727Notes

Reaction equation

HRID 1644727 reaction equation
C(N(CC)CC)C.[CH2:8]([O:10][C:11](=[O:41])[CH2:12][C:13]1[CH:22]=[C:21]([C:23](=[O:39])[C:24]2[CH:29]=[CH:28][C:27]([S:30]([N:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)(=[O:32])=[O:31])=[CH:26][CH:25]=2)[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([F:40])[CH:19]=2)[CH:14]=1)[CH3:9].Cl[C:43]([O:45][CH2:46][CH3:47])=[O:44]>ClCCl>[CH2:46]([O:45][C:43]([N:36]1[CH2:37][CH2:38][N:33]([S:30]([C:27]2[CH:26]=[CH:25][C:24]([C:23]([C:21]3[C:20]4[C:15](=[CH:16][CH:17]=[C:18]([F:40])[CH:19]=4)[CH:14]=[C:13]([CH2:12][C:11]([O:10][CH2:8][CH3:9])=[O:41])[CH:22]=3)=[O:39])=[CH:29][CH:28]=2)(=[O:31])=[O:32])[CH2:34][CH2:35]1)=[O:44])[CH3:47]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 59350847HCID 59350847, compound

Product 1

HCID 59350824HCID 59350824, compoundYield 41.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (0.19 mL, 1.34 mmol) was added slowly at 0° C. to a stirred reaction mixture of {6-fluoro-4-[4-(piperazine-1-sulfonyl)-benzoyl]-naphthalen-2-yl}-acetic acid ethyl ester (0.200 g, 0.33 mmol, prepared as described above) in dichloromethane (7 mL). The reaction mixture was stirred at room temperature for 15 minutes. Ethyl chloroformate (0.07 mL, 0.73 mmol) was added slowly to the reaction mixture and stirring was continued for an additional 3 hours at room temperature. The mixture was diluted with dichloromethane (10 mL), then washed with a saturated solution of sodium bicarbonate (5 mL) and water (5 mL). The organic layer was collected, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel (100-200 mesh) column chromatography (1:3 ethyl acetate -hexane) to give 0.077 g (41.4%) of 4-[4-(3-ethoxycarbonylmethyl-7-fluoro-naphthalene-1-carbonyl)-benzenesulfonyl]-piperazine-1-carboxylic acid ethyl ester as a viscous yellow solid. MS cald. for C28H29FN2O7S ([M+H]+) 556, obsd. 557.2.

Workup

  1. stirringstirring
  2. waitwas continued for an additional 3 hours at room temperature
  3. washwashed with a saturated solution of sodium bicarbonate (5 mL) and water (5 mL)
  4. customThe organic layer was collected
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by silica gel (100-200 mesh) column chromatography (1:3 ethyl acetate -hexane)

Sources & evidence

ORD record
ord-e8ebbaaec00b49aaa8f4df426c3c740d
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

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