Trifluoroacetic acid → HCID 14732723, compound

HRID 358029Notes

Reaction equation

HRID 358029 reaction equation
FC(F)(F)C(O)=O.[C:8]([O:11][CH2:12][C:13]1[CH2:14][S:15][C@@H:16]2[C@H:27]([NH:28][C:29](=[O:68])/[C:30](=[N:56]\[O:57][C:58]([C:61]([O:63]C(C)(C)C)=[O:62])([CH3:60])[CH3:59])/[C:31]3[N:32]=[C:33]([NH:36]C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[S:34][CH:35]=3)[C:26](=[O:69])[N:17]2[C:18]=1[C:19]([O:21]C(C)(C)C)=[O:20])(=[O:10])[CH3:9]>C1(OC)C=CC=CC=1>[C:8]([O:11][CH2:12][C:13]1[CH2:14][S:15][C@@H:16]2[C@H:27]([NH:28][C:29](=[O:68])/[C:30](/[C:31]3[N:32]=[C:33]([NH2:36])[S:34][CH:35]=3)=[N:56]\[O:57][C:58]([C:61]([OH:63])=[O:62])([CH3:60])[CH3:59])[C:26](=[O:69])[N:17]2[C:18]=1[C:19]([OH:21])=[O:20])(=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 15573431HCID 15573431, compound

Product 1

HCID 14732723HCID 14732723, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

Trifluoroacetic acid (18 ml) was added to a solution of the product of Stage (a) (2.4 g) in anisole (18 ml) at 0°. The mixture was stirred at room temperature for 2 hours and concentrated. The residue was dissolved in ethyl acetate and extracted with saturated sodium bicarbonate solution. The pH of the aqueous extracts was adjusted to 6, and the solution washed with ethyl acetate. The aqueous phase was acidified to pH 1.5 under ethyl acetate, saturated with sodium chloride, and extracted with ethyl acetate. The combined organic extracts were washed with saturated brine, dried and evaporated. The residue was dissolved in warm 50% aqueous formic acid (20 ml) and allowed to stand for 2 hours. The mixture was diluted with water (50 ml, and filtered. The filtrate was concentrated. The residue was taken up in water (50 ml), refiltered, and lyophilized to give the title compound (920 mg), λmax (pH 6 buffer) 236 nm (E1 cm1% 250), λinf 255 nm (E1 cm1% 235), 296 nm (E1 cm1% 103); [α]D20 +20.0° (c 1.0, DMSO).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. extractionextracted with saturated sodium bicarbonate solution
  4. washthe solution washed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThe combined organic extracts were washed with saturated brine
  7. customdried
  8. customevaporated
  9. dissolutionThe residue was dissolved in warm 50% aqueous formic acid (20 ml)
  10. waitto stand for 2 hours
  11. additionThe mixture was diluted with water (50 ml
  12. filtrationfiltered
  13. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-c52e3cd5c682424e8a6c017860a42acf
Source dataset
uspto-grants-1984_08
Patent number
US04464368

Reaction notes

Loading…