Triethylamine → 3-hydroxy-N-(2-nitrobenzyl)-3-phenyl propionic acid amide

HRID 553402

Reaction equation

HRID 553402 reaction equation
Cl.[N+:2]([C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7][NH2:8])([O-:4])=[O:3].[OH:13][CH:14]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:15][C:16](O)=[O:17].C(N(CC)CC)C.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.O.Cl>O1CCCC1>[OH:13][CH:14]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:15][C:16]([NH:8][CH2:7][C:6]1[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=1[N+:2]([O-:4])=[O:3])=[O:17]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 929593-Hydroxy-3-phenylpropanoic acidHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 12235442(2-Nitrophenyl)methanamine hydrochlorideHCID 21885828Hydrate;hydrochloride

Product 1

HCID 674618943-hydroxy-N-(2-nitrobenzyl)-3-phenyl propionic acid amideYield 92.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Nitrobenzyl amine hydrochloride (2.27 g, 12.0 mmol), 3-hydroxy-3-phenyl propionic acid (2.00 g, 12.0 mmol), triethylamine (1.34 g, 13.3 mmol) were added to tetrahydrofuran (50 ml) and the reaction mixture was ice cooled. Under ice cooled condition, 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (3.33 g, 12.0 mmol) was added thereto and stirred at room temperature for five hours. The reaction mixture was poured into dilute hydrochloric acid water and extracted with ethyl acetate. The organic layer was washed with a saturated brine and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained crude crystal was washed with a mixture of hexane-ether (2:1) to obtain 3-hydroxy-N-(2-nitrobenzyl)-3-phenyl propionic acid amide (3.32 g).

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with a saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained crude crystal
  7. washwas washed with a mixture of hexane-ether (2:1)

Sources & evidence

ORD record
ord-fc313c2da70d4e3490790ff94c8806ae
Source dataset
uspto-grants-2011_11
Patent number
US08048825B2

Linked notes

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