Acetone → HCID 59692692, compound

HRID 898859Notes

Reaction equation

HRID 898859 reaction equation
[C:1]([O:5][C:6]([C:8]1([NH:19][S:20]([C:23]2[S:24][C:25]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)=[CH:26][CH:27]=2)(=[O:22])=[O:21])[CH2:10][C:9]1([CH2:17][NH2:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:35][C:36]([CH3:38])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>O1CCCC1.C(O)(=O)C>[C:1]([O:5][C:6]([C:8]1([NH:19][S:20]([C:23]2[S:24][C:25]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)=[CH:26][CH:27]=2)(=[O:22])=[O:21])[CH2:10][C:9]1([CH2:17][NH:18][CH:36]([CH3:38])[CH3:35])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 180AcetoneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 59693008HCID 59693008, compound

Product 1

HCID 59692692HCID 59692692, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the obtained 2-aminomethyl-1-[5-(4-chloro-phenyl)-thiophene-2-sulfonylamino]-2-phenyl-cyclopropanecarboxylic acid t-butyl ester (60 mg, 0.12 mmol) in tetrahydrofuran (1.0 mL) were added acetone (13 μL, 0.17 mmol) and sodium triacetoxyborohydride (37 mg, 0.17 mmol) at 0° C. under argon atmosphere, and the mixture was stirred at room temperature for 20 hours. To the obtained solution was added acetic acid (50 μL), and the mixture was further stirred for 21 hours. Then saturated aqueous sodium hydrogen carbonate solution (2.0 mL) was added and the aqueous layer was extracted with ethyl acetate (3.0 mL). The organic layer was washed with water (2.0 mL) and saturated aqueous sodium chloride solution (2.0 mL), and dried over magnesium sulfate. After filtration and evaporation, the obtained residue was purified by silica gel chromatography (chloroform:methanol=25:2) to give the title compound (45 mg, yield 69%) as a pale-yellow oil.

Workup

  1. stirringthe mixture was further stirred for 21 hours
  2. extractionthe aqueous layer was extracted with ethyl acetate (3.0 mL)
  3. washThe organic layer was washed with water (2.0 mL) and saturated aqueous sodium chloride solution (2.0 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtration and evaporation
  6. customthe obtained residue was purified by silica gel chromatography (chloroform:methanol=25:2)

Sources & evidence

ORD record
ord-f5e7d0c132c04adf9faf26d657b3227d
Source dataset
uspto-grants-2008_04
Patent number
US07351825B2

Reaction notes

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