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

HRID 278064Notes

Reaction equation

HRID 278064 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-1544d341db0846a290fdee2ca39fffce
Source dataset
uspto-grants-2002_03
Patent number
US06358992B1

Reaction notes

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