Phthalic Anhydride → HCID 178465696, compound

HRID 967227Notes

Reaction equation

HRID 967227 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10](=[O:28])[N:11]([CH2:13][CH2:14][C@H:15]2[CH2:20][CH2:19][C@H:18]([CH2:21][N:22]([CH2:26][CH3:27])[CH2:23][CH2:24][OH:25])[CH2:17][CH2:16]2)[CH3:12])=[CH:5][CH:4]=1.C1(=O)OC(=[O:35])C2=CC=CC=C12.OO.NC(N)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl.CCOCC.O>[CH2:26]([N+:22]([CH2:23][CH2:24][OH:25])([CH2:21][C@H:18]1[CH2:19][CH2:20][C@H:15]([CH2:14][CH2:13][N:11]([CH3:12])[C:10]([O:9][C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:29])([F:30])[F:1])=[CH:4][CH:5]=2)=[O:28])[CH2:16][CH2:17]1)[O-:35])[CH3:27]

Participants

7

Reactant 4

HCID 6811Phthalic Anhydride2×HCID 31294Carbamide Peroxide2×HCID 516892Sodium BicarbonateHCID 178464463HCID 178464463, compound

Product 1

HCID 178465696HCID 178465696, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21584184Diethylether waterSolvent

Procedure

A mixture of 702 mg (1.63 mmol) [trans-(2-(4-{[ethyl-(2-hydroxy-ethyl)-amino]-methyl}-cyclohexyl)-ethyl]-methyl-carbamic acid 4-trifluoromethyl-phenyl ester, 256.6 mg (1.8 mmol) of phthalic anhydride and 335 mg (3.54 mmol) of Hydrogen peroxide•Urea adduct in 7 ml of CH2Cl2, was stirred for two days at RT. Additional 100 mg (1.06 mmol) of Hydrogen peroxide•Urea adduct and 50 mg (0.34 mmol) of phthalic anhydride were added to the reaction mixture. After another 3 h at RT, 10 ml of aqueous saturated NaHCO3 were added. After stirring for 10 min at RT, the reaction-mixture was taken up in ether/water. The ether phase was dried and evaporated under reduced pressure. The residue was chromatographed on silica gel with a 9:1 v/v mixture of methylenchloide/methanol as eluent giving 449 mg (62%) of pure rac-trans-ethyl(2-hydroxyethyl)({4-[2-(methyl{[4-(trifluoromethyl)phenoxy]carbonyl}amino)ethyl]cyclohexyl}methyl)ammoniumolate, MS: 447 (MH+).

Workup

  1. waitAfter another 3 h at RT
  2. stirringAfter stirring for 10 min at RT
  3. dry with materialThe ether phase was dried
  4. customevaporated under reduced pressure
  5. customThe residue was chromatographed on silica gel with a 9:1 v/v mixture of methylenchloide/methanol as eluent

Sources & evidence

ORD record
ord-12e7268cb48f4c79a9938a5cb4a063df
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

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