Potassium Carbonate → (R)-2-Hydroxy-N-(4-nitrophenethyl)-2-phenylacetamide

HRID 1392374Notes

Reaction equation

HRID 1392374 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][NH2:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:13](O)(=[O:22])[C@@H:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[OH:15].C(=O)([O-])[O-].[K+].[K+].OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC>O.CN(C)C=O>[OH:15][C@H:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:13]([NH:12][CH2:11][CH2:10][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)=[O:22]

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 11914(-)-Mandelic acidHCID 951534-NitrophenethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 178418300HCID 178418300, compound

Product 1

HCID 59678380(R)-2-Hydroxy-N-(4-nitrophenethyl)-2-phenylacetamideYield 87.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 9.77 g of 4-nitrophenylethylamine 1/2 sulfate, 6.00 g of (R)-mandelic acid, 4.70 g of potassium carbonate and 60 mL of N,N-dimethylformamide, 6.14 g of hydroxybenztriazole and 8.70 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide monohydrochloride (EDC) were added, and the mixture was stirred at around room temperature for 2 hours. 0.87 g of EDC was further added, and the mixture was stirred at around room temperature overnight. The reaction solution was diluted with water and extracted with ethyl acetate. The organic layer was washed successively with 1M hydrochloric acid aqueous solution, 20% potassium carbonate aqueous solution and water, and then concentrated in vacuo. The residue was recrystallized from toluene to obtain 10.4 g of (R)-2-hydroxy-N-[2-(4-nitrophenyl)ethyl]-2-phenylacetamide as a pale yellow crystal.

Workup

  1. additionwere added
  2. stirringthe mixture was stirred at around room temperature overnight
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed successively with 1M hydrochloric acid aqueous solution, 20% potassium carbonate aqueous solution and water
  5. concentrationconcentrated in vacuo
  6. customThe residue was recrystallized from toluene

Sources & evidence

ORD record
ord-82177b2151ae4cee9791adcbcaa740f2
Source dataset
uspto-grants-2008_03
Patent number
US07342117B2

Reaction notes

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