Tetrahydrofuran → HCID 22467258, compound

HRID 381317Notes

Reaction equation

HRID 381317 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([C:26]3[C:34]4[C:29](=[CH:30][C:31](/[CH:35]=[CH:36]/[C:37]([OH:39])=[O:38])=[CH:32][CH:33]=4)[N:28]([CH3:40])[CH:27]=3)[C:11]([NH:13][S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH:23]([CH3:25])[CH3:24])=[CH:19][CH:18]=3)(=[O:16])=[O:15])=[O:12])=[CH:9][C:4]=2[O:3][CH2:2]1.C([O-])=O.[NH4+].O1CCCC1>[Pd].C(O)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([C:26]3[C:34]4[C:29](=[CH:30][C:31]([CH2:35][CH2:36][C:37]([OH:39])=[O:38])=[CH:32][CH:33]=4)[N:28]([CH3:40])[CH:27]=3)[C:11]([NH:13][S:14]([C:17]3[CH:18]=[CH:19][C:20]([CH:23]([CH3:25])[CH3:24])=[CH:21][CH:22]=3)(=[O:15])=[O:16])=[O:12])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 2723923Ammonium formateHCID 22467199HCID 22467199, compound2×

Product 1

HCID 22467258HCID 22467258, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Palladium-on-carbon (10 mg) was added to a stirred solution of (E)-3-[3-{1-(1,3-benzodioxol-5-yl)-2-[(4-isopropylphenyl)sulfonamido]-2-oxoethyl}-1-methyl-1H-6-indolyl]-2-propenoic acid (the compound of Example 58, 80 mg, 0.14 mmol) and ammonium formate (64 mg, 0.5 mmol) in a 1:1 mixture of tetrahydrofuran and ethanol (10 ml total). The mixture was stirred at reflux for 48 h. cooled, filtered through Arbocel™ and concentrated. The grey foam was purified by flash column chromatography (elution with 98% dichloromethane/2% methanol) giving the product as a white foam.

Workup

  1. temperatureat reflux for 48 h.
  2. temperaturecooled
  3. filtrationfiltered through Arbocel™
  4. concentrationconcentrated
  5. customThe grey foam was purified by flash column chromatography (elution with 98% dichloromethane/2% methanol)

Sources & evidence

ORD record
ord-6f6ede1591434e10a123eb85d07d0efe
Source dataset
uspto-grants-2001_10
Patent number
US06306852B1

Reaction notes

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