Tetrahydrofuran → HCID 57239333, compound

HRID 1488813Notes

Reaction equation

HRID 1488813 reaction equation
[CH2:1]([NH:10][C:11]1[C:19]2[C:14](=[CH:15][C:16]([C:20]([F:23])([F:22])[F:21])=[CH:17][CH:18]=2)[NH:13][C:12]=1[C:24]([O:26]CC)=[O:25])[C:2](C1C=CC=CC=1)=O.C(OC(OC(C)(C)C)=O)(O[C:32](C)([CH3:34])[CH3:33])=O.[O:44]1[CH2:48][CH2:47][CH2:46][CH2:45]1.CN(C1C=CC=CN=1)C>C(OCC)(=O)C>[CH2:2]([CH2:1][NH:10][C:11]1[C:19]2[C:14](=[CH:15][C:16]([C:20]([F:21])([F:22])[F:23])=[CH:17][CH:18]=2)[NH:13][C:12]=1[C:24]([OH:26])=[O:25])[C:48]([C:47]1[CH:34]=[CH:32][CH:33]=[CH:45][CH:46]=1)=[O:44]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 218852-DimethylaminopyridineHCID 90495Di-tert-butyl dicarbonateHCID 21460729HCID 21460729, compound

Product 1

HCID 57239333HCID 57239333, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Mix 3-[(phenacyl)amino]-2-carbethoxy-6-trifluoromethylindole (390 mg, 1.04 mmol), di-tert-butyl dicarbonate (249 mg, 1.14 mmol), tetrahydrofuran (10 mL), dimethylaminopyridine (33 mg, 0.32 mmol) and stir overnight. Dilute the reaction with ethyl acetate, wash with 1M HCl, water, dry over magnesium sulfate, filter and concentrate in vacuo. Purify by flash chromatography (15% ethyl acetate/hexane) to yield the title compound as an amber oil (320 mg, 66%).

Workup

  1. additionDilute
  2. washwash with 1M HCl, water
  3. dry with materialdry over magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify by flash chromatography (15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2c5e844b764445b288c788a2d2ea9707
Source dataset
uspto-grants-1997_10
Patent number
US05675018

Reaction notes

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