Sodium Bicarbonate → HCID 87619092, compound

HRID 2111429Notes

Reaction equation

HRID 2111429 reaction equation
[CH:1]1([NH:6][CH:7]2[CH2:11][CH2:10][CH2:9][CH:8]2[C:12]([O:14][CH3:15])=[O:13])[CH2:5][CH2:4][CH2:3][CH2:2]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-].[Na+]>C(OCC)(=O)C>[CH3:15][O:14][C:12]([CH:8]1[CH2:9][CH2:10][CH2:11][CH:7]1[N:6]([C:19]1[C:20]([N+:24]([O-:26])=[O:25])=[CH:21][N:22]=[C:17]([Cl:16])[N:18]=1)[CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1)=[O:13]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 57635049HCID 57635049, compound

Product 1

HCID 87619092HCID 87619092, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To an ice cooled solution of 9.56 g (0.045 mole) of (rac)-2-cyclopentylamino-cyclopentanecarboxylic acid, methyl ester and 200 mL of ethyl acetate was added 9.5 g (0.0475 mole) of 2,4-dichloro-5-nitro-pyrimidine and 9.6 g (0.113 mole) of sodium bicarbonate. The mixture was heated overnight at 65 degrees, then cooled and washed with water, extracting the aqueous layer twice with ethyl acetate. The combined ethyl acetate layers were washed successively with water, then brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromography, eluting with hexanes-ethyl acetate (100:0-80:20), to give 11.4 g of (rac)-2-[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]-cyclopentanecarboxylic acid methyl ester (IV-68).

Workup

  1. temperatureThe mixture was heated overnight at 65 degrees
  2. temperaturecooled
  3. washwashed with water
  4. extractionextracting the aqueous layer twice with ethyl acetate
  5. washThe combined ethyl acetate layers were washed successively with water
  6. dry with materialbrine, dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel chromography
  10. washeluting with hexanes-ethyl acetate (100:0-80:20)

Sources & evidence

ORD record
ord-983f9c3342834cc3958f9c78546e88df
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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