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Triethylamine → (RS)-2-(4-chlorobenzenesulfonylamino)-N-(4-(ethoxycarbonylmethyl)phenyl)butanamide

HRID 266358
Notes
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Reaction equation

HRID 266358 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:12][CH:11]=1.[I-].C[N+]1C=CC=CC=1Cl.[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([S:38]([NH:41][CH:42]([CH2:46][CH3:47])[C:43](O)=[O:44])(=[O:40])=[O:39])=[CH:34][CH:33]=1>C(Cl)(Cl)Cl>[Cl:31][C:32]1[CH:33]=[CH:34][C:35]([S:38]([NH:41][CH:42]([CH2:46][CH3:47])[C:43]([NH:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:14][CH:15]=2)=[O:44])(=[O:39])=[O:40])=[CH:36][CH:37]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 3266285(RS)-2-(4-chlorobenzenesulfonylamino)butanoic acidHCID 24192282Ethyl (4-aminophenyl)acetate--hydrogen chloride (1/1)

Product 1

HCID 19032983(RS)-2-(4-chlorobenzenesulfonylamino)-N-(4-(ethoxycarbonylmethyl)phenyl)butanamideYield 16.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Triethylamine (1.99 ml), ethyl 4-aminophenylacetate hydrochloride (699 mg), and 1-methyl-2-chloropyridinium iodide (1.1 g) were added to a solution of (RS)-2-(4-chlorobenzenesulfonylamino)butanoic acid (1 g) in chloroform (30 ml), and the whole was heated under reflux for 2 hours under argon. The reaction mixture was concentrated under reduced pressure. After adding 1N HCl, the residue was extracted with ethyl acetate. The combined ethyl acetate layers were washed with a saturated saline solution, and dried over Na2SO4. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 70 g, hexane/ethyl acetate=2/1) to give (RS)-2-(4-chlorobenzenesulfonylamino)-N-(4-(ethoxycarbonylmethyl) phenyl)butanamide (237 mg).

Workup

  1. temperaturethe whole was heated
  2. temperatureunder reflux for 2 hours under argon
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionAfter adding 1N HCl
  5. extractionthe residue was extracted with ethyl acetate
  6. washThe combined ethyl acetate layers were washed with a saturated saline solution
  7. dry with materialdried over Na2SO4
  8. customThe solvent was evaporated under reduced pressure
  9. customThe residue was purified by column chromatography (silica gel 70 g, hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-a74198e9447c4141b53b3f8232f4f299
Source dataset
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05650428

Reaction notes

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