Trifluoroacetic acid → HCID 21254065, compound

HRID 1531558Notes

Reaction equation

HRID 1531558 reaction equation
C(OC(=O)[N:7]([CH2:23][CH2:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([NH:34][C:35]3[O:36][C:37]([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)=[CH:38][N:39]=3)[CH:32]=2)[NH:27][C:26]=1[C:46]1[CH:51]=[C:50]([CH3:52])[CH:49]=[C:48]([CH3:53])[CH:47]=1)[CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[CH:14][CH:13]=1)(C)(C)C.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>>[CH3:52][C:50]1[CH:51]=[C:46]([C:26]2[NH:27][C:28]3[C:33]([C:25]=2[CH2:24][CH2:23][NH:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([NH:18][S:19]([CH3:22])(=[O:20])=[O:21])=[CH:16][CH:17]=2)=[CH:32][C:31]([NH:34][C:35]2[O:36][C:37]([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)=[CH:38][N:39]=2)=[CH:30][CH:29]=3)[CH:47]=[C:48]([CH3:53])[CH:49]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 70226148HCID 70226148, compound

Product 1

HCID 21254065HCID 21254065, compoundYield 92.4%

Conditions

Temperature
0 °C

Procedure

To a solution of {2-[2-(3,5-dimethylphenyl)-5-(5-phenyloxazol-2-ylamino)-1H-indol-3-yl]-ethyl}-[4-(4-methanesulfonylaminophenyl)butyl]-carbamic acid tert-butyl ester (10 mg in 0.80 mL methylene chloride) at 0° C. was added 0.050 mL anisole followed by 0.20 mL trifluoroacetic acid and the mixture stirred at 0° C. After 3 hours, the mixture was concentrated in vacuo and the residual acid removed by azeotrope with toluene. Purification of the concentrate by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 90:7:1) gave the title compound (8 mg). m/e 648 (M+H)

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customthe residual acid removed by azeotrope with toluene
  3. customPurification of the
  4. concentrationconcentrate by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 90:7:1)

Sources & evidence

ORD record
ord-cd6dcf4295da4ce0ae244ba3a4a9e5b6
Source dataset
uspto-grants-2001_03
Patent number
US06197975B1

Reaction notes

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