Trifluoroacetic acid → HCID 19024447, compound

HRID 1033804Notes

Reaction equation

HRID 1033804 reaction equation
C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][N:22]([CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[C:23]([N:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:27][CH2:26]2)=[O:24])=[CH:17][CH:16]=1)(=[O:8])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>C1(OC)C=CC=CC=1>[CH2:34]([N:22]([CH2:21][C:18]1[CH:17]=[CH:16][C:15]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[S:6](=[O:7])(=[O:8])[NH2:5])=[CH:20][CH:19]=1)[C:23]([N:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][CH2:26]1)=[O:24])[CH2:35][CH2:36][CH2:37][CH3:38]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 19024465HCID 19024465, compound

Product 1

HCID 19024447HCID 19024447, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

A solution of 59 mg (0.11 mmole) of 1-[N-[[2'-(N-t-butylsulfamoyl)biphenyl-4-yl]methyl]-N-pentylcarbamoyl]indoline (from Step A), 20 μL of anisole, and 0.5 mL of anhydrous TFA was stirred at room temperature for 16 hours. The residue obtained after evaporation of excess TFA was flash chromatographed over silica gel (elution with 0.5% MeOH--CH2Cl2) to give 49 mg (89%) of the title compound as a hard gum, homogeneous by TLC (95:5 MeOH--CH2Cl2); FAB-MS m/e 478 (M+1)+.

Workup

  1. customThe residue obtained
  2. customafter evaporation of excess TFA
  3. customchromatographed over silica gel (elution with 0.5% MeOH--CH2Cl2)

Sources & evidence

ORD record
ord-f8a109c4019646889469825aa4eb75f0
Source dataset
uspto-grants-1994_05
Patent number
US05312820

Reaction notes

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