Sodium Bicarbonate → HCID 69629173, compound

HRID 987330Notes

Reaction equation

HRID 987330 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C@H:19]([O:23][CH2:24][CH3:25])[C:20]([OH:22])=[O:21])=[CH:14][CH:13]=2)=[CH:5][CH:4]=1.C(=O)([O-])O.[Na+].[F:31][C:32]([F:44])([F:43])[S:33][C:34]1[CH:39]=[CH:38][C:37]([N:40]=[C:41]=[O:42])=[CH:36][CH:35]=1.CO.ClCCl>O1CCCC1>[CH2:24]([O:23][C@@H:19]([CH2:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:10][CH2:9][C:6]2[CH:5]=[CH:4][C:3]([NH:2][C:41]([NH:40][C:37]3[CH:38]=[CH:39][C:34]([S:33][C:32]([F:43])([F:31])[F:44])=[CH:35][CH:36]=3)=[O:42])=[CH:8][CH:7]=2)=[CH:13][CH:14]=1)[C:20]([OH:22])=[O:21])[CH3:25]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 27333921-Isocyanato-4-[(trifluoromethyl)sulfanyl]benzeneHCID 21226129Dichloromethane methanolHCID 86595065HCID 86595065, compound

Product 1

HCID 69629173HCID 69629173, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-{4-[2-(4-Aminophenyl)ethoxy]phenyl}-(S)-2-ethoxypropanoic acid hydro chloride (described in Example 56a) (0.2 g; (0.547 mmole) was dissolved in tetrahydrofuran (5 ml). Sodium hydrogencarbonate (0.051 g; 0.607 mmole) was added and the mixture was stirred for a little while. 4-(Trifluoromethylthio)phenyl isocyanate (0.126 g; 0.575 mmole) was added. The reaction mixture was stirred at room temperature for 6 hours and then evaporated to dryness. Ethyl acetate and water were added to the residue and the phases were separated. The organic phase was dried with magnesium sulfate and the solvent was evaporated. Chromatography of residue on silica gel (isolute, SI) using dichloromethane, methanol:dichloromethane (1:99) and then methanol:dichloromethane (2:98) as eluants gave 0.17 g (57% yield) of (S)-2-ethoxy-3-[4-(2-{4-[({4-[(trifluoromethyl)sulfanyl]anilino}carbonyl)amino]phenyl}ethoxy)phenyl]propanoic acid.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 6 hours
  2. customevaporated to dryness
  3. additionEthyl acetate and water were added to the residue
  4. customthe phases were separated
  5. dry with materialThe organic phase was dried with magnesium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-e3ee2f4384b94cd4ab8f38750f0d97a0
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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