Sodium Bicarbonate → HCID 86637517, compound

HRID 1676818Notes

Reaction equation

HRID 1676818 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C:5]([F:18])([F:17])[CH2:6][NH:7][C@@H:8]1[CH2:10][C@H:9]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:2].[Cl:20][C:21]1[N:26]=[C:25](Cl)[C:24]([N+:28]([O-:30])=[O:29])=[CH:23][N:22]=1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:19])[C:5]([F:18])([F:17])[CH2:6][N:7]([C:23]1[C:24]([N+:28]([O-:30])=[O:29])=[CH:25][N:26]=[C:21]([Cl:20])[N:22]=1)[C@@H:8]1[CH2:10][C@H:9]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 67076250HCID 67076250, compound

Product 1

HCID 86637517HCID 86637517, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 7.8 g (0.029 mole) of 2,2-difluoro-3-(trans-2-phenyl-cyclopropylamino)-propionic acid ethyl ester in 20 mL of ethyl acetate was added over 5 minutes to a cooled (0 degrees) mixture of 5.6 g (0.029 mole) of 2,4-dichloro-5-nitro-pyrimidine, 9.7 g (0.12 mole) of sodium bicarbonate and 80 mL of ethyl acetate. The cooling bath was removed and the mixture stirred for 17 hours at room temperature. Activated charcoal was added and after stirring briefly, the mixture was filtered through a pad of Celite, washing the filter pad with ethyl acetate. The filtrate was concentrated under reduced pressure to give 11.8 g of 3-[(2-chloro-5-nitro-pyrimidin-4-yl)-(trans-2-phenyl-cyclopropyl)-amino]-2,2-difluoro-propionic acid ethyl ester (IV-287) as a yellow thick oil.

Workup

  1. temperaturea cooled
  2. customThe cooling bath was removed
  3. additionActivated charcoal was added
  4. stirringafter stirring briefly
  5. filtrationthe mixture was filtered through a pad of Celite
  6. washwashing the filter pad with ethyl acetate
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6fcb1d442bf44730a831355275eed4c6
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Reaction notes

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