Tetrahydrofuran → HCID 58929558, compound

HRID 46109Notes

Reaction equation

HRID 46109 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-09a24d2fc5974914ad652c3f29b6e174
Source dataset
uspto-grants-2013_09
Patent number
US08541592B2

Reaction notes

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