Trifluoroacetic acid → HCID 11599367, compound

HRID 2222957Notes

Reaction equation

HRID 2222957 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][C@H:18]([N:31]2[C:35](=[O:36])[CH:34]([C:37]3[CH:46]=[CH:45][C:40]4[O:41][CH2:42][CH2:43][O:44][C:39]=4[CH:38]=3)[NH:33][C:32]2=[O:47])[C:19](=[O:30])[NH:20][C:21]2[S:22][CH:23]=[C:24]([C:26]([O:28][CH3:29])=[O:27])[N:25]=2)=[CH:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:29][O:28][C:26]([C:24]1[N:25]=[C:21]([NH:20][C:19](=[O:30])[C@@H:18]([N:31]2[C:35](=[O:36])[CH:34]([C:37]3[CH:46]=[CH:45][C:40]4[O:41][CH2:42][CH2:43][O:44][C:39]=4[CH:38]=3)[NH:33][C:32]2=[O:47])[CH2:17][C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[NH:8][CH:9]=2)[S:22][CH:23]=1)=[O:27]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86604044HCID 86604044, compound

Product 1

HCID 11599367HCID 11599367, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold solution of 3-[(S)-2-[4-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-2,5-dioxo-imidazolidin-1-yl]-2-(4-methoxycarbonyl-thiazol-2-ylcarbamoyl)-ethyl]-indole-1-carboxylic acid tert-butyl ester (78 mg, 0.118 mmol) in dichloromethane (10 mL), was added trifluoroacetic acid (2 mL, 26.0 mmol). The reaction mixture was stirred at room temperature for 1 hour. The volatiles were removed in vacuo and the residue was dissolved in ethyl acetate (100 mL), washed once with cold saturated aqeous sodium bicarbonate, water, brine and dried over sodium sulfate. The solvent was removed and the residue was purified by chromatographed over silica gel gradient eluted between 50% and 75% ethyl acetate in hexanes to afford 2-[(S)-2-[4-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-2,5-dioxo-imidazolidin-1-yl]-3-(1H-indol-3-yl)-propionylamino]-thiazole-4-carboxylic acid methyl ester (37 mg, 55%).

Workup

  1. customThe volatiles were removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
  3. washwashed once with cold saturated aqeous sodium bicarbonate, water, brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed
  6. customthe residue was purified
  7. customby chromatographed over silica gel gradient
  8. washeluted between 50% and 75% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-c5d2ee4b569e439c8b5a2411f8d5c587
Source dataset
uspto-grants-2008_05
Patent number
US07371869B2

Reaction notes

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