Tetrahydrofuran → HCID 57901795, compound

HRID 1851454Notes

Reaction equation

HRID 1851454 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][C:15]([C:18]([O:20]CC)=[O:19])=[CH:14]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].O1CCCC1>C(O)C>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][C:15]([C:18]([OH:20])=[O:19])=[CH:14]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57901606HCID 57901606, compound

Product 1

HCID 57901795HCID 57901795, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of ethyl 7-[(tert-butoxycarbonyl)amino]-1H-indole-2-carboxylate (2.65 g), 1N aqueous sodium hydroxide solution (22.0 mL), tetrahydrofuran (20 mL) and ethanol (30 mL) was stirred at 50° C. for 3 hr. The reaction mixture was concentrated, and water was added to the residue. The mixture was acidified with 10% aqueous citric acid solution, and the resulting crystals were filtrated, washed with water, and dried to give the title compound (2.27 g, yield 94%) as colorless crystals. melting point>246° C. (decomposition).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added to the residue
  3. filtrationthe resulting crystals were filtrated
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-155ac59809124c508f54abeb0b525c1f
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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