Trifluoroacetic acid → HCID 87179034, compound

HRID 386755Notes

Reaction equation

HRID 386755 reaction equation
Cl.C1(C2C=CC=CC=2)[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:14](=[O:15])[C:13]([C:16]([NH:18][CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])=[O:17])=[C:12]([OH:27])[C:11]3[CH2:28][NH:29][CH2:30][C:10]2=3)=[CH:4][CH:3]=1.[Cl:37][C:38]1[CH:45]=[CH:44][C:41]([CH2:42]Br)=[CH:40][CH:39]=1.[C:46]([OH:52])([C:48]([F:51])([F:50])[F:49])=[O:47]>C(Cl)Cl>[F:49][C:48]([F:51])([F:50])[C:46]([O-:52])=[O:47].[Cl:37][C:38]1[CH:45]=[CH:44][C:41]([CH2:42][NH+:29]2[CH2:28][C:11]3[C:12]([OH:27])=[C:13]([C:16]([NH:18][CH2:19][C:20]([OH:22])=[O:21])=[O:17])[C:14](=[O:15])[N:9]([CH2:8][C:5]4[CH:6]=[CH:7][C:46]([C:48]([F:51])([F:50])[F:49])=[CH:3][CH:4]=4)[C:10]=3[CH2:30]2)=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 66850853HCID 66850853, compound

Product 1

HCID 87179034HCID 87179034, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Intermediate 6, compound 6-1, (50 mg, 0.11 mmol) was dissolved in DCM (1 mL) and 4-chlorobenzylbromide (22 mg, 0.11 mmol) and TEA (0.045 mL, 0.32 mmol) were added and the mixture was refluxed for 24 h. The reaction was cooled to rt and TFA (0.5 mL, 6 mmol) was added and the solution was stirred an additional 30 min. The reaction was concentrated and the residue was purified on a C-18 reverse phase chromatography column eluted with 0-90% MeCN in water. The desired fractions were lyophilized overnight affording the title compound, E39-1. 535.8 (M+1); Rt=2.80 min.

Workup

  1. temperaturethe mixture was refluxed for 24 h
  2. concentrationThe reaction was concentrated
  3. customthe residue was purified on a C-18 reverse phase chromatography column
  4. washeluted with 0-90% MeCN in water
  5. waitThe desired fractions were lyophilized overnight

Sources & evidence

ORD record
ord-93f90adb98a4499e948c5fc0fc1faf77
Source dataset
uspto-grants-2013_02
Patent number
US08372863B2

Reaction notes

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