Trifluoroacetic acid → HCID 9847163, compound

HRID 1884398Notes

Reaction equation

HRID 1884398 reaction equation
CN(C([O:8][N:9]1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1.Cl.C(ON)(C)(C)C.[Cl:37][C:38]1[CH:43]=[CH:42][C:41]([C:44]2[CH:49]=[CH:48][C:47]([S:50]([CH2:53][CH:54]([CH2:58][S:59][C:60]3[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=3)[C:55](O)=[O:56])(=[O:52])=[O:51])=[CH:46][CH:45]=2)=[CH:40][CH:39]=1.FC(F)(F)C(O)=O>CN(C=O)C.C(#N)C.C(OCC)(=O)C>[Cl:37][C:38]1[CH:43]=[CH:42][C:41]([C:44]2[CH:49]=[CH:48][C:47]([S:50]([CH2:53][CH:54]([CH2:58][S:59][C:60]3[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=3)[C:55]([NH:9][OH:8])=[O:56])(=[O:52])=[O:51])=[CH:46][CH:45]=2)=[CH:40][CH:39]=1

Participants

9

Reactant 5

HCID 6422Trifluoroacetic acidHCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 9824852HCID 9824852, compound

Product 1

HCID 9847163HCID 9847163, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-5 °C

Procedure

TBTU (0,72 g) was added portionwise to a stirred solution of N-methylmorpholine (0.5 mL) and O-tert-butylhydroxylamine hydrochloride (0.43 g) and 3-[(4′-chloro[1,1′-biphenyl]-4-yl)sulfonyl]-2-[(phenylsulfanyl)methyl]-propanoic acid (0.5 g) in 20 mL of DMF and 20 mL of acetonitrile cooled at −5° C. After stirring at ambient temperature overnight, the resulting solution was diluted with ethyl acetate and sequentially washed with 0.1 M citric acid and 0.1 M NaHCO3. After drying over anhydrous sodium sulfate and removal of the solvent, the crude reaction mixture was treated with trifluoroacetic acid (10 mL) and kept aside for 6 hours. The solvent was removed and the residue was partitioned between ethyl acetate and 0.1 M NaHCO3. After drying, the solvent was evaporated off and the residue was chromatographed on silica gel eluting with chloroform/cyclohexane 2/3 to afford, after crystallization from ethyl acetate, 0.35 g of the title compound, mp . . .

Workup

  1. washsequentially washed with 0.1 M citric acid and 0.1 M NaHCO3
  2. dry with materialAfter drying over anhydrous sodium sulfate and removal of the solvent
  3. customthe crude reaction mixture
  4. waitkept aside for 6 hours
  5. customThe solvent was removed
  6. customthe residue was partitioned between ethyl acetate and 0.1 M NaHCO3
  7. customAfter drying
  8. customthe solvent was evaporated off
  9. customthe residue was chromatographed on silica gel eluting with chloroform/cyclohexane 2/3
  10. customto afford
  11. customafter crystallization from ethyl acetate, 0.35 g of the title compound

Sources & evidence

ORD record
ord-e7df02fbde0547768d909d67fca62e8d
Source dataset
uspto-grants-2004_07
Patent number
US06765003B1

Reaction notes

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