Methyl 3-benzyloxycarbonylamino-4-(1-pentynyl)benzoate → HCID 53794293, compound

HRID 1108678Notes

Reaction equation

HRID 1108678 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][C:21]=1[C:22]#[C:23][CH2:24][CH2:25][CH3:26])[C:15]([O:17][CH3:18])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCCC1.[Cl-].[Na+].[Au+3].[Cl-].[Cl-].[Cl-]>[CH2:1]([O:8][C:9]([N:11]1[C:12]2[C:21](=[CH:20][CH:19]=[C:14]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=2)[CH:22]=[C:23]1[CH2:24][CH2:25][CH3:26])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 22627418Methyl 3-benzyloxycarbonylamino-4-(1-pentynyl)benzoate

Product 1

HCID 53794293HCID 53794293, compoundYield 89.8%

Reagents, catalysts & solvents 2

HCID 9928900AuCl4NaCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-benzyloxycarbonylamino-4-(1-pentynyl)benzoate (949 mg) in tetrahydrofuran (24 ml) was added gold(III)sodium chloride (24 mg) under argon atmosphere, and the mixture was heated under reflux for 100 minutes. The solvent was evaporated in vacuo and the residue was chromatographed on silica gel eluting with a mixture of hexane, dichloromethane, and ethyl acetate (6:3:2) to give methyl 1-benzyloxycarbonyl-2-propylindole-6-carboxylate (852 mg) as colorless crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 100 minutes
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was chromatographed on silica gel eluting with a mixture of hexane, dichloromethane, and ethyl acetate (6:3:2)

Sources & evidence

ORD record
ord-b1157839ecbd4d4594b3d7f08fa1c45e
Source dataset
uspto-grants-2000_05
Patent number
US06069156

Reaction notes

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