Potassium Bicarbonate → (Rac)-2-{[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]-methyl}-pentanoic acid ethyl ester

HRID 2111295Notes

Reaction equation

HRID 2111295 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH:5]([CH2:9][NH:10][CH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)[CH2:6][CH2:7][CH3:8])[CH3:2].[Cl:17][C:18]1[N:23]=[C:22](Cl)[C:21]([N+:25]([O-:27])=[O:26])=[CH:20][N:19]=1.C(=O)(O)[O-].[K+]>O.C(OCC)C>[CH2:1]([O:3][C:4](=[O:16])[CH:5]([CH2:9][N:10]([C:20]1[C:21]([N+:25]([O-:27])=[O:26])=[CH:22][N:23]=[C:18]([Cl:17])[N:19]=1)[CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15]1)[CH2:6][CH2:7][CH3:8])[CH3:2]

Participants

6

Reactant 3

HCID 516893Potassium BicarbonateHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 57635032(Rac)-2-cyclopentylaminomethyl-pentanoic acid ethyl ester

Product 1

HCID 87618409(Rac)-2-{[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]-methyl}-pentanoic acid ethyl esterYield 72.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 1.14 g (0.005 mole) of (rac)-2-cyclopentylaminomethyl-pentanoic acid ethyl ester in 25 mL of water was added dropwise to a solution of 0.97 g (0.005 mole) of 2,4-dichloro-5-nitro-pyrimidine in 25 mL of ethyl ether. At 0 degrees, 1.0 g (0.010 mole) of potassium bicarbonate was added. The mixture was stirred at ambient temperature for 3 hours. The layers were then separated, and the aqueous layer extracted twice with 30 mL of ether. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Purification by silica gel chromatography, eluting with hexanes-ethyl acetate (100:0-80:20) gave 1.4 g of (rac)-2-{[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]-methyl}-pentanoic acid ethyl ester (IV-16).

Workup

  1. customThe layers were then separated
  2. extractionthe aqueous layer extracted twice with 30 mL of ether
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by silica gel chromatography
  7. washeluting with hexanes-ethyl acetate (100:0-80:20)

Sources & evidence

ORD record
ord-481d7382797e42eb80261c94a9bbdfe8
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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