Trifluoroacetic acid → HCID 22877422, compound

HRID 1740250Notes

Reaction equation

HRID 1740250 reaction equation
C(OC([NH:8][C:9]([CH3:47])([CH2:45]C)[C:10]([NH:12][C@@H:13]1[CH2:19][CH2:18][C:17]2[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=2[N:15]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[CH2:37][NH:38][C:39]([NH:41][CH3:42])=[O:40])=[CH:27][C:26]=2[Br:43])[C:14]1=[O:44])=[O:11])=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl.C1(OC)C=CC=CC=1>[NH2:8][C:9]([CH3:47])([CH3:45])[C:10]([NH:12][C@@H:13]1[CH2:19][CH2:18][C:17]2[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=2[N:15]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[CH2:37][NH:38][C:39]([NH:41][CH3:42])=[O:40])=[CH:27][C:26]=2[Br:43])[C:14]1=[O:44])=[O:11]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22877448HCID 22877448, compound

Product 1

HCID 22877422HCID 22877422, compoundYield 69.6%

Reagents, catalysts & solvents 2

HCID 7519AnisoleCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 146 mg (0.211 mmol) of 2-t-butoxycarbonylamino-2-methyl-N-[2,3,4,5-tetrahydro-1-[[2'-[[[(methylamino)carbonyl]amino]methyl]-3-bromo-[1,1'-biphenyl]-4-yl]methyl]-2-oxo-1H-benzazepin-3(R)-yl]butanamide (Step L) in 5 L of methylene chloride was added 5 drops of anisole followed by 5 mL of trifluoroacetic acid. The reaction mixture was stirred at room temperature for 1 hour then the solvent was removed under vacuum. The residue was purified by reverse phase medium pressure liquid chromatography on C-8, eluting with methanol/0.1% aqueous trifluoroacetic acid (60:40), to afford 87 mg (58%) of the title compound as a white solid. 1H NMR (200 MHz, CD3OD): δ 1.52 (s, 3H), 1.59 (s, 3H), 2.32 (m, 2H), 2.60-3.02 (m, 2H), 2.65 (s, 3H), 4.17 (dd; 18, 14 Hz; 2H), 4.43 (dd; 12, 9 Hz; 1H), 4.90 (d, 16 Hz, 4H), 5.34 (d, 16 Hz, 2H), 7.10-7.42 (m, 8H), 7.50 (m, 3H). FAB-MS: calculated for C30H34BrN5O3 592; found 593, 595 (100%).

Workup

  1. customthe solvent was removed under vacuum
  2. customThe residue was purified by reverse phase medium pressure liquid chromatography on C-8
  3. washeluting with methanol/0.1% aqueous trifluoroacetic acid (60:40)

Sources & evidence

ORD record
ord-6d0b1b7722e847ce902023ee88ce1db5
Source dataset
uspto-grants-1999_10
Patent number
US05968924

Reaction notes

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