Trifluoroacetic acid → HCID 178521270, compound

HRID 1584035Notes

Reaction equation

HRID 1584035 reaction equation
FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1.COC1C=CC(C[O:23][NH:24][C:25](=[O:33])[CH2:26][N:27]2[C:31]([SH:32])=[N:30][N:29]=[N:28]2)=CC=1>>[SH:32][C:31]1[N:27]([CH2:26][C:25]([NH:24][OH:23])=[O:33])[N:28]=[N:29][N:30]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 178491620HCID 178491620, compound

Product 1

HCID 178521270HCID 178521270, compoundYield 102.8%

Procedure

To a mixed solvent of trifluoroacetic acid (15 ml) and anisole (15 ml) is added 5-mercapto-1H-tetrazole-1-acetohydroxamic acid p-methoxybenzyl ester (3 g), and the mixture is stirred at room temperature for 2 hours under nitrogen gas. The reaction mixture is concentrated under reduced pressure, and the resultant material is dissolved in water and passed through a column of synthetic resin adsorbent (Diaion HP-20 distributed by Mitsubishi Chemical K.K.) (95 ml). The resin is washed with water. The fractions containing the main product are combined and concentrated under reduced pressure. The resultant solid is crystallized from a mixture of ether and hexane to give the title compound (1.83 g). mp. 105°-107° C.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. dissolutionthe resultant material is dissolved in water
  3. washThe resin is washed with water
  4. additionThe fractions containing the main product
  5. concentrationconcentrated under reduced pressure
  6. customThe resultant solid is crystallized from a mixture of ether and hexane

Sources & evidence

ORD record
ord-cecea1614b3c4484b5631d323a74f4cb
Source dataset
uspto-grants-1985_11
Patent number
US04555578

Reaction notes

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