Trifluoroacetic acid → HCID 58246486, compound

HRID 2090597Notes

Reaction equation

HRID 2090597 reaction equation
[N:1]1[CH:5]=[C:4]([CH2:6][C@H:7]([NH:35]C(=O)OC(C)(C)C)[C:8](=[O:34])[N:9]2[CH2:14][CH2:13][CH:12]([C:15]3[S:16][CH:17]=[C:18]([C:20]4[CH:29]=[CH:28][C:27]5[C:26]([CH3:31])([CH3:30])[CH2:25][CH2:24][C:23]([CH3:33])([CH3:32])[C:22]=5[CH:21]=4)[N:19]=3)[CH2:11][CH2:10]2)[NH:3][CH:2]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:35][C@@H:7]([CH2:6][C:4]1[NH:3][CH:2]=[N:1][CH:5]=1)[C:8]([N:9]1[CH2:14][CH2:13][CH:12]([C:15]2[S:16][CH:17]=[C:18]([C:20]3[CH:29]=[CH:28][C:27]4[C:26]([CH3:31])([CH3:30])[CH2:25][CH2:24][C:23]([CH3:32])([CH3:33])[C:22]=4[CH:21]=3)[N:19]=2)[CH2:11][CH2:10]1)=[O:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58246455HCID 58246455, compound

Product 1

HCID 58246486HCID 58246486, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

250 mg (0.42 mmol) of tert-butyl ((S)-1-(3H-imidazol-4-ylmethyl)-2-oxo-2-{4-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]-piperidin-1-yl}ethyl)carbamate are dissolved in 20 ml of dichloromethane and 1 ml of trifluoroacetic acid and stirred at room temperature for 12 h. The reaction mixture is washed with 0.1 N NaOH, the organic phase is dried over sodium sulfate and purified by column chromatography on silica gel. The crude product is dissolved in acetone, and a pH of 4 is set using 1 N HCl. A white precipitate forms in the process, which is filtered off with suction, washed with ether and dried in vacuo. Yield: 200 mg of “A63” hydrochloride, white solid; ESI: 492 (M+H).

Workup

  1. washThe reaction mixture is washed with 0.1 N NaOH
  2. dry with materialthe organic phase is dried over sodium sulfate
  3. custompurified by column chromatography on silica gel
  4. dissolutionThe crude product is dissolved in acetone
  5. filtrationA white precipitate forms in the process, which is filtered off with suction
  6. washwashed with ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-e616cfc68cf74ee1b07cb0d64709ed01
Source dataset
uspto-grants-2013_05
Patent number
US08436186B2

Reaction notes

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