Tetrahydrofuran → HCID 58929558, compound

HRID 2360271Notes

Reaction equation

HRID 2360271 reaction equation
C([NH:9][C:10]([NH:12][C@H:13]1[CH2:18][C@H:17]2[CH2:19][C@@H:14]1[CH2:15][C:16]2([F:21])[F:20])=[S:11])(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].O1CCCC1>CO.O>[F:21][C:16]1([F:20])[CH2:15][C@H:14]2[CH2:19][C@@H:17]1[CH2:18][C@@H:13]2[NH:12][C:10]([NH2:9])=[S:11]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 58929843HCID 58929843, compound

Product 1

HCID 58929558HCID 58929558, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 1-benzoyl-3-((1R,2S,4R)-5,5-difluorobicyclo-[2.2.1]heptan-2-yl)thiourea (˜1.80 mmol) and potassium carbonate (1.49 g, 10.8 mmol) in methanol (5.0 mL), water (2.5 mL), and tetrahydrofuran (2.5 mL) was stirred at ambient temperature for 2 h. The reaction mixture was concentrated in vacuo, and the residue was partitioned between EtOAc and water. The organic portion was washed with brine, conc. in vacuo, and purified by flash column chromatography (0 to 65% of ethyl acetate in hexanes) to give the title compound as a white solid. MS m/z: 207.0 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between EtOAc and water
  3. washThe organic portion was washed with brine, conc. in vacuo
  4. custompurified by flash column chromatography (0 to 65% of ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-d74ec451d7b344e184dd4469302bd347
Source dataset
uspto-grants-2014_04
Patent number
US08686011B2

Reaction notes

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