Tetrahydrofuran → HCID 86612303, compound

HRID 253161Notes

Reaction equation

HRID 253161 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:15])=[O:5])[CH3:2].O1CCCC1.C(=O)([O-])[O-].[K+].[K+].Cl[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29]>O>[C:32]1([CH2:31][O:30][C:28]([NH:15][C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:8]=2[NH:7][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:14]3)=[O:29])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 111381941H-Indole-2-carboxylic acid, 7-amino-, ethyl ester

Product 1

HCID 86612303HCID 86612303, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

0.8 g (3.925 mmol) of 7-amino-1H-indole-2-carboxylic acid ethyl ester are mixed with 16 ml of tetrahydrofurane and 1.08 g (7.83 mmol) of potassium carbonate. The reaction medium is cooled to 0° C. and 0.615 ml (4.30 mmol) of benzyl chloroformate are added. Agitation is performed for 1 hour 30 minutes at 0° C., and then the temperature of the mixture is allowed to rise again to ambient temperature over one hour. Then 30 ml of water are added and the product is extracted using ethyl acetate. The combined organic phases are dried on magnesium sulfate, filtered and concentrated under reduced pressure. The evaporation residue is purified by silica column chromatography eluting with the help of a methylcyclohexane/ethyl acetate mixture (90/1; v/v). The expected product is obtained in the form of white crystals with a yield of 61%.

Workup

  1. waitto rise again to ambient temperature over one hour
  2. extractionthe product is extracted
  3. customThe combined organic phases are dried on magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe evaporation residue is purified by silica column chromatography
  7. washeluting with the help of a methylcyclohexane/ethyl acetate mixture (90/1; v/v)

Sources & evidence

ORD record
ord-6ed29a9bcd6445a4a35aa177d382a27d
Source dataset
uspto-grants-2011_01
Patent number
US07872021B2

Reaction notes

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