Methyl 2-methyl-3-[(phenylmethyl)amino]propanoate → HCID 87617944, compound

HRID 2111343Notes

Reaction equation

HRID 2111343 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH:4]([CH3:14])[CH2:5][NH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl:16][C:17]1[N:22]=[C:21](Cl)[C:20]([N+:24]([O-:26])=[O:25])=[CH:19][N:18]=1.C(=O)(O)[O-].[K+]>C(OCC)(=O)C.O>[CH3:1][O:2][C:3](=[O:15])[CH:4]([CH3:14])[CH2:5][N:6]([CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:19]1[C:20]([N+:24]([O-:26])=[O:25])=[CH:21][N:22]=[C:17]([Cl:16])[N:18]=1

Participants

6

Reactant 3

HCID 97781Methyl 2-methyl-3-[(phenylmethyl)amino]propanoateHCID 516893Potassium BicarbonateHCID 5212662,4-Dichloro-5-nitropyrimidine

Product 1

HCID 87617944HCID 87617944, compoundYield 69.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of 2.73 g (0.010 mole) of (rac)-3-benzylamino-2-methyl-propanoic acid methyl ester, 1.84 g (0.010 mole) of 2,4-dichloro-5-nitro-pyrimidine, 50 mL of ethyl acetate and 25 mL of water was added 3.0 g (0.030 mole) of potassium bicarbonate. The mixture was stirred for 3 hours, then diluted with 50 mL of ethyl acetate and 50 mL of water. The layers were separated, and the aqueous layer extracted twice with 100 mL of ethyl acetate. The organic layers were washed with 100 mL of brine, combined, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with dichloromethane-ethyl acetate (100:0-97:3) to give 2.55 g of (rac)-3-[benzyl-(2-chloro-5-nitro-pyrimidin-4-yl)-amino]-2-methyl-propanoic acid methyl ester (IV-42) as pale yellow oil.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer extracted twice with 100 mL of ethyl acetate
  3. washThe organic layers were washed with 100 mL of brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with dichloromethane-ethyl acetate (100:0-97:3)

Sources & evidence

ORD record
ord-208ab84748304e679a14ab5cbfddaf05
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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