Trifluoroacetic acid → HCID 59822268, compound

HRID 1670561Notes

Reaction equation

HRID 1670561 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([CH2:20][S:21][C:22]3[S:23][CH2:24][CH2:25][N:26]=3)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:19][C:16]1[CH:17]=[CH:18][C:11]2[CH2:10][CH2:9][NH:8][CH2:14][CH2:13][C:12]=2[C:15]=1[CH2:20][S:21][C:22]1[S:23][CH2:24][CH2:25][N:26]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67337074HCID 67337074, compound

Product 1

HCID 59822268HCID 59822268, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-tert-butoxycarbonyl-7-chloro-6-(4,5-dihydro-thiazol-2-ylthiomethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (0.77 g, 1.9 mmol) in anhydrous DCM (41 mL) at room temperature add trifluoroacetic acid (37.7 mL) and stir the solution at room temperature overnight. Concentrate in vacuo and elute the residue through a SCX column (10 g). Dissolve the residue in DCM, load the solution on to a RediSep® column (40 g) and purify the crude mixture by preparative liquid chromatography (linear gradient: 100:0 to 90:10 DCM/2M ammonia in methanol over 30 min; 35 mL/min) to afford 7-chloro-6-(4,5-dihydro-thiazol-2-ylthiomethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (0.58 g, 100%). MS (ES+) m/z: 313.1 (M+H)+.

Workup

  1. concentrationConcentrate in vacuo
  2. washelute the residue through a SCX column (10 g)
  3. dissolutionDissolve the residue in DCM
  4. customload the solution on to a RediSep® column (40 g) and purify the crude mixture by preparative liquid chromatography (linear gradient: 100:0 to 90:10 DCM/2M ammonia in methanol over 30 min; 35 mL/min)

Sources & evidence

ORD record
ord-959d5be764a44e8fa44771aa8d69b771
Source dataset
uspto-grants-2011_08
Patent number
US07994163B2

Reaction notes

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