Trifluoroacetic acid → HCID 59534031, compound

HRID 1697272Notes

Reaction equation

HRID 1697272 reaction equation
FC(F)(F)C(O)=O.C(OC([NH:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH:22]=[C:21]([N:26]([CH2:38][P:39](=[O:46])([O:43][CH2:44][CH3:45])[O:40][CH2:41][CH3:42])[S:27]([C:30]1[CH:35]=[C:34]([Cl:36])[CH:33]=[C:32]([Cl:37])[CH:31]=1)(=[O:29])=[O:28])[CH:20]=[CH:19]2)=O)(C)(C)C.[OH-].[Na+]>C(Cl)Cl>[NH2:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH:22]=[C:21]([N:26]([CH2:38][P:39](=[O:46])([O:40][CH2:41][CH3:42])[O:43][CH2:44][CH3:45])[S:27]([C:30]1[CH:35]=[C:34]([Cl:36])[CH:33]=[C:32]([Cl:37])[CH:31]=1)(=[O:29])=[O:28])[CH:20]=[CH:19]2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 59533983HCID 59533983, compound

Product 1

HCID 59534031HCID 59534031, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 ml trifluoroacetic acid is pipetted into 130 mg diethyl {[(6-tert.-butoxycarbonylamino-naphthalen-2-yl)-(3,5-dichloro-phenylsulphonyl)-amino]-methyl}-phosphonate in 3 ml methylene chloride. The reaction mixture is stirred for two and a half hours at ambient temperature, then made alkaline with 1 N sodium hydroxide solution and extracted with methylene chloride. The combined organic phases are washed with 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).

Workup

  1. extractionextracted with methylene chloride
  2. washThe combined organic phases are washed with saturated sodium chloride solution
  3. customdried on magnesium sulphate
  4. customevaporated down
  5. customThe flask residue is chromatographed through a silica gel column with cyclohexane/ethyl acetate (40:60 to 0:100)

Sources & evidence

ORD record
ord-db54b6cb3d424a2d80a5c0e7b976e92c
Source dataset
uspto-grants-2012_04
Patent number
US08163911B2

Reaction notes

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