HCID 16097175, compound → HCID 22626323, compound

HRID 277978Notes

Reaction equation

HRID 277978 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:12]=1[C:20]1[C:21]([C:26]([OH:28])=[O:27])=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)S(OC1C=CC([N+]([O-])=O)=CC=1C(OCC1C=CC=CC=1)=O)(=O)=O>>[CH2:1]([O:8][C:9]([C:11]1[CH:16]=[C:15]([NH2:17])[CH:14]=[CH:13][C:12]=1[C:20]1[C:21]([C:26]([OH:28])=[O:27])=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 16097175HCID 16097175, compoundHCID 17809339HCID 17809339, compound

Product 1

HCID 22626323HCID 22626323, compoundYield 55.9%

Procedure

To a solution of 2′-benzyloxycarbonyl-4′-nitro-2-biphenylcarboxylic acid (2.08 g) which was prepared by the same procedure as a series of reaction of Reference Example 4→Reference Example 5, using Benzyl 2-trifluoromethylsulfonyloxy-5-nitrobenzoate, in concentration hydrochloric acid-ethanol (5:3, 8 ml), a solution of Tin (II) chloride dihydrate (3.7 g) in ethanol (5 ml) was added. The mixture was stirred for 1 hour at room temperature. 2N aqueous solution of sodium hydroxide was added to the reaction solution, the solution was extracted with ethyl acetate (2 times). The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (Chloroform:Methanol:Water=9:1:0.1→8:2:0.2) to give the title compound (1.07 g) having the following physical data.

Workup

  1. concentrationin concentration hydrochloric acid-ethanol (5:3, 8 ml)
  2. additiona solution of Tin (II) chloride dihydrate (3.7 g) in ethanol (5 ml) was added
  3. addition2N aqueous solution of sodium hydroxide was added to the reaction solution
  4. extractionthe solution was extracted with ethyl acetate (2 times)
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel (Chloroform:Methanol:Water=9:1:0.1→8:2:0.2)

Sources & evidence

ORD record
ord-5ed7382d8b9343d1927f0cea65b70b65
Source dataset
uspto-grants-2002_03
Patent number
US06358960B1

Reaction notes

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