Trifluoroacetic acid → HCID 21191156, compound

HRID 1069088Notes

Reaction equation

HRID 1069088 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][CH2:19][NH:20]C(OC(C)(C)C)=O)[CH:12]=2)[CH:8]=[CH:9][CH:10]=1)=[O:4].FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][CH2:19][NH2:20])[CH:12]=2)[CH:8]=[CH:9][CH:10]=1)=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 54336416HCID 54336416, compound

Product 1

HCID 21191156HCID 21191156, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The methyl-3′-[2-[[(tert-butoxy)carbonyl]amino]ethoxy]-[1,1′-biphenyl]-3-carboxylate (659 mg) was dissolved in methylene chloride (25 mL) and trifluoroacetic acid (2.5 mL) was added. The mixture was stirred at room temperature for 6 h, additional trifluoroacetic acid (1.0 mL) was added and the mixture was stirred overnight. The mixture was concentrated and partitioned between saturated aqueous sodium bicarbonate and ethyl acetate. The organic layer was separated, dried over sodium sulfate, filtered and concentrated to give the crude product. This residue was partitioned between 1:1 hexane: ethyl acetate and 1 N aqueous HCl. The aqueous layer was separated, washed with 1:1 hexane: ethyl acetate and made basic by addition of solid sodium bicarbonate. The mixture was extracted twice with ethyl acetate, and the combined organic extracts were dried over sodium sulfate, filtered and concentrated to afford the title compound (474 mg) as a colorless oil. Electrospray MS (positive ion): (M+H) 272.0.

Workup

  1. stirringthe mixture was stirred overnight
  2. concentrationThe mixture was concentrated
  3. custompartitioned between saturated aqueous sodium bicarbonate and ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude product
  9. customThis residue was partitioned between 1:1 hexane
  10. customThe aqueous layer was separated
  11. washwashed with 1:1 hexane
  12. additionethyl acetate and made basic by addition of solid sodium bicarbonate
  13. extractionThe mixture was extracted twice with ethyl acetate
  14. dry with materialthe combined organic extracts were dried over sodium sulfate
  15. filtrationfiltered
  16. concentrationconcentrated

Sources & evidence

ORD record
ord-66f9ec29f64b4aac90bd651018e8bb33
Source dataset
uspto-grants-2001_06
Patent number
US06251925B1

Reaction notes

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