Triethylamine → (RS)-2-(4-chlorobenzenesulfonylamino)-N-(4-(2-methoxycarbonylethyl) phenyl)-3-phenylpropanamide

HRID 266379Notes

Reaction equation

HRID 266379 reaction equation
C([N:3]([CH2:6][CH3:7])CC)C.[C:8](Cl)(=O)C(C)(C)C.Cl[C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH:25][CH:26]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:27]([OH:29])=O)(=[O:24])=[O:23])=[CH:18][CH:17]=1.[ClH:37].N[C:39]1[CH:44]=[CH:43][C:42]([CH:45](C)[C:46]([O:48][CH3:49])=[O:47])=CC=1>C1COCC1>[Cl:37][C:16]1[CH:17]=[CH:18][C:19]([S:22]([NH:25][CH:26]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:27]([NH:3][C:6]2[CH:7]=[CH:8][C:43]([CH2:42][CH2:45][C:46]([O:48][CH3:49])=[O:47])=[CH:44][CH:39]=2)=[O:29])(=[O:23])=[O:24])=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 27650422-{[(4-Chlorophenyl)sulfonyl]amino}-3-phenylpropanoic acidHCID 15580485Methyl 2-(4-aminophenyl)propanoate hydrochloride

Product 1

HCID 19032737(RS)-2-(4-chlorobenzenesulfonylamino)-N-(4-(2-methoxycarbonylethyl) phenyl)-3-phenylpropanamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (480 μl) and pivaloyl chloride (175 μl) were added to a solution of (RS)-2-(4-chlorobenzenesulfonylamino)-3-phenylpropanoic acid (301.7 mg) in THF (5 ml), and the whole was stirred for 2 hours. After methyl 4-aminophenylpropionate hydrochloride (229.8 mg) was added, the whole was stirred at room temperature overnight. The reaction mixture was poured into a saturated saline solution and 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 to obtain a yellow oil. The product was purified by column chromatography (silica gel 50 g, hexane/ethyl acetate=3/1) to obtain (RS)-2-(4-chlorobenzenesulfonylamino)-N-(4-(2-methoxycarbonylethyl) phenyl)-3-phenylpropanamide (40.4 mg).

Workup

  1. stirringthe whole was stirred at room temperature overnight
  2. additionThe reaction mixture was poured into a saturated saline solution
  3. extractionextracted with ethyl acetate
  4. washThe combined ethyl acetate layers were washed with a saturated saline solution
  5. dry with materialdried over Na2SO4
  6. customThe solvent was evaporated under reduced pressure
  7. customto obtain a yellow oil
  8. customThe product was purified by column chromatography (silica gel 50 g, hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-626128010c8a48c58f9124c0c966205a
Source dataset
uspto-grants-1997_07
Patent number
US05650428

Reaction notes

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