Triethylamine → HCID 22927019, compound

HRID 1985421Notes

Reaction equation

HRID 1985421 reaction equation
[C:1]([CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([CH2:14][CH:15]([O:21][CH:22]([CH3:24])[CH3:23])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:6]1)(O)=[O:2].C(N(CC)CC)C.ClC(OCC)=O>O1CCCC1>[OH:2][CH2:1][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([CH2:14][CH:15]([O:21][CH:22]([CH3:23])[CH3:24])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 22926821HCID 22926821, compound

Product 1

HCID 22927019HCID 22927019, compoundYield 49.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

0.3 g of Ethyl 3-(1-carboxymethyl-1H-indol-3-yl)-2-isopropoxypropionate was dissolved in 10 ml of tetrahydrofuran, and 0.2 ml of triethylamine was added under ice-cooling, followed by 0.1 ml of ethyl chloroformate, then the mixture was stirred at 0° C. for 15 minutes. After filtering off the precipitated insoluble substances, the reaction solution was again cooled with ice, and 60 mg of sodium borohydride and water were added, and stirring was continued at room temperature for 1 hour. The reaction solution was cooled with ice, acidified with diluted hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and evaporated. The residue was subjected to silica gel column chromatography (33% ethyl acetate-hexane), to give 143 mg of the title compound.

Workup

  1. temperaturecooling
  2. filtrationAfter filtering off the precipitated insoluble substances
  3. temperaturethe reaction solution was again cooled with ice, and 60 mg of sodium borohydride and water
  4. additionwere added
  5. stirringstirring
  6. waitwas continued at room temperature for 1 hour
  7. temperatureThe reaction solution was cooled with ice
  8. extractionextracted with ethyl acetate
  9. washThe organic layer was washed with saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customevaporated

Sources & evidence

ORD record
ord-da069425df1e4fd79d8e85a6a5d10e95
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

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