Trifluoroacetic acid → HCID 55290747, compound

HRID 2111677Notes

Reaction equation

HRID 2111677 reaction equation
FC(F)(F)C(O)=O.[OH:8][CH2:9][C:10]1[CH:14]=[C:13]([CH2:15][NH:16]C(OC(C)(C)C)=O)[O:12][N:11]=1>C(Cl)Cl>[NH3:11].[OH:8][CH2:9][C:10]1[CH:14]=[C:13]([CH2:15][NH2:16])[O:12][N:11]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67284568543713-48-0

Product 2

HCID 222AmmoniaHCID 55290747HCID 55290747, compoundYield 195.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (4 ml, 54 mmol) was added to a solution of 3-hydroxymethyl-5-[N-(tert-butyloxycarbonyl)aminomethyl]isoxazole (Method 75; 1.25 g, 5.4 mmol) in DCM (40 ml). The mixture was stirred at ambient temperature for 18 hours then the volatiles removed by evaporation. The residue was purified by chromatography on a SCX-2 column (50 g) eluting with methanol then 7N ammonia in methanol to give the title compound (676 mg, 96%). NMR (DMSO): 1.97 (br s, 2H), 3.76 (s, 2H), 4.44 (s, 2H), 5.38 (s, 1H), 6.26 (s, 1H).

Workup

  1. customthe volatiles removed by evaporation
  2. customThe residue was purified by chromatography on a SCX-2 column (50 g)
  3. washeluting with methanol

Sources & evidence

ORD record
ord-90c1ead4e53a4e3489884b94115bed20
Source dataset
uspto-grants-2009_04
Patent number
US07521453B2

Reaction notes

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