Trifluoroacetic acid → HCID 11027869, compound

HRID 1264577Notes

Reaction equation

HRID 1264577 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[N:15]([C:23](=[O:34])[C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=3)[CH2:14][CH:13]2[C:35]([O:37]C(C)(C)C)=[O:36])(=[O:11])=[O:10])=[CH:5][CH:4]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([N:12]2[CH2:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[N:15]([C:23](=[O:34])[C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:31])([F:32])[F:33])[CH:25]=3)[CH2:14][CH:13]2[C:35]([OH:37])=[O:36])(=[O:11])=[O:10])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86755437HCID 86755437, compound

Product 1

HCID 11027869HCID 11027869, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.36 g (0.61 mmol) of 4-(4-methoxybenzenesulfonyl)-1-(3-trifluoromethylbenzoyl)-2,3,4,5-tetrahydro-1H-[1,4]benzodiazepine-3-carboxylic acid, tert-butyl ester and 3 ml of trifluoroacetic acid in 3 ml of CH2Cl2 was stirred at room temperature for 3 hours. The mixture was concentrated to dryness under vacuum and the residue extracted with CH2Cl2. The CH2Cl2 was washed with 1 N NaHCO3 and the aqueous layer (pH 8) was acidified with 2 N citric acid and extracted with ethyl acetate. The extract was dried (Na2SO4). The original CH2Cl2 extract was washed with 2 N citric acid, H2O, brine and dried with Na2SO4. The CH2Cl2 extract and the ethyl acetate extract were combined and the solvent removed under vacuum to give 0.31 g of solid, m.p. 105-110° C. Anal. for C25H21F3N2O6S: Calc'd: C, 56.2; H, 4.0; N, 5.2; Found: C, 55.1; H, 3.7; N, 5.0.

Workup

  1. concentrationThe mixture was concentrated to dryness under vacuum
  2. extractionthe residue extracted with CH2Cl2
  3. washThe CH2Cl2 was washed with 1 N NaHCO3
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract was dried (Na2SO4)
  6. extractionThe original CH2Cl2 extract
  7. washwas washed with 2 N citric acid, H2O, brine
  8. dry with materialdried with Na2SO4
  9. extractionThe CH2Cl2 extract
  10. extractionthe ethyl acetate extract
  11. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-33f14e8fe41743539362100b5226002a
Source dataset
uspto-grants-2003_04
Patent number
US06544984B1

Reaction notes

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