Benzyl Alcohol → HCID 22627421, compound

HRID 278091Notes

Reaction equation

HRID 278091 reaction equation
[C:1]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15]([OH:17])=[O:16])=[CH:12][CH:13]=2)[NH:8][C:7]=1[CH2:18][CH2:19][CH3:20])(=[O:5])[CH:2]([CH3:4])[CH3:3].[CH2:21](O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1.CN(C)C1C=CN=CC=1>[C:1]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15]([O:17][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:16])=[CH:12][CH:13]=2)[NH:8][C:7]=1[CH2:18][CH2:19][CH3:20])(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 10868DicyclohexylcarbodiimideHCID 22627341HCID 22627341, compound

Product 1

HCID 22627421HCID 22627421, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a stirred solution of 3-isobutyryl-2-propylindole-6-carboxylic acid (331 mg) in tetrahydrofuran (5 ml) were added benzylalcohol (1.25 ml), dicyclohexylcarbodiimide (303 mg) and 4-dimethylaminopyridine (20 mg) at 20° C. The reaction mixture was stirred at 20° C. for 8 hours. The precipitated urea was filtered off and the filtrate was evaporated in vacuo. The residue was extracted with ethyl acetate and the extract was washed with water two times and brine. The organic phase was dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:4) to give the crystals which were recrystallized from a mixture of ethyl acetate and hexane to give benzyl 3-isobutyryl-2-propylindole-6-carboxylate (215 mg) as colorless crystals.

Workup

  1. filtrationThe precipitated urea was filtered off
  2. customthe filtrate was evaporated in vacuo
  3. extractionThe residue was extracted with ethyl acetate
  4. washthe extract was washed with water two times and brine
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:4)
  8. customto give the crystals which
  9. customwere recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-9a7aeea3f3954b29991c4c9aa06937ab
Source dataset
uspto-grants-2002_03
Patent number
US06358992B1

Reaction notes

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