Ethyl Acetate → Diethyl {[(5-benzylaminocarbonyl-naphthalen-2-yl)-(3,5-dichloro-phenylsulphonyl)-amino]-methyl}-phosphonate

HRID 1697269Notes

Reaction equation

HRID 1697269 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[C:20]2[C:15](=[CH:16][C:17]([NH:21][S:22]([C:25]3[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[CH:26]=3)(=[O:24])=[O:23])=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:33]([O:35][P:36]([CH2:41]OS(C(F)(F)F)(=O)=O)([O:38][CH2:39][CH3:40])=[O:37])[CH3:34].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[CH2:1]([NH:8][C:9]([C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:20]=1[CH:19]=[CH:18][C:17]([N:21]([CH2:41][P:36](=[O:37])([O:38][CH2:39][CH3:40])[O:35][CH2:33][CH3:34])[S:22]([C:25]1[CH:26]=[C:27]([Cl:32])[CH:28]=[C:29]([Cl:31])[CH:30]=1)(=[O:24])=[O:23])=[CH:16]2)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 11833487(Diethoxyphosphoryl)methyl trifluoromethanesulfonateHCID 595341116-(3,5-Dichloro-phenylsulphonylamino)-naphthalene-1-carboxylic acid-benzylamide

Product 1

HCID 59534062Diethyl {[(5-benzylaminocarbonyl-naphthalen-2-yl)-(3,5-dichloro-phenylsulphonyl)-amino]-methyl}-phosphonate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 200 mg 6-(3,5-dichloro-phenylsulphonylamino)-naphthalene-1-carboxylic acid-benzylamide, 180 mg diethylphosphonomethyltriflate (prepared analogously to Tetrahedron Letters 1986, 27, 1477) and 100 mg potassium carbonate in 4 ml N,N-dimethylformamide is stirred for three hours at ambient temperature. Then it is combined with ethyl acetate, washed with water and saturated sodium chloride solution, dried on magnesium sulphate and evaporated down. The flask residue is chromatographed through a silica gel column with cyclohexane/ethyl acetate (40:60 to 0:100) as eluant.

Workup

  1. washwashed with water and saturated sodium chloride solution
  2. customdried on magnesium sulphate
  3. customevaporated down
  4. customThe flask residue is chromatographed through a silica gel column with cyclohexane/ethyl acetate (40:60 to 0:100) as eluant

Sources & evidence

ORD record
ord-6b5cab20bbf840b58689520996118b3b
Source dataset
uspto-grants-2012_04
Patent number
US08163911B2

Reaction notes

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