Chlorosuccinimide → HCID 178501072, compound

HRID 1893347Notes

Reaction equation

HRID 1893347 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]2[CH:15]=[C:14]([CH3:16])[O:13][N:12]=2)[CH2:7][CH2:6]1)=[O:4].[Cl:17]N1C(=O)CCC1=O>CN(C)C=O>[CH3:1][O:2][C:3]([C@H:5]1[CH2:6][CH2:7][C@H:8]([C:11]2[C:15]([Cl:17])=[C:14]([CH3:16])[O:13][N:12]=2)[CH2:9][CH2:10]1)=[O:4]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 178501043HCID 178501043, compound

Product 1

HCID 178501072HCID 178501072, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of trans-4-(5-methyl-isoxazol-3-yl)-cyclohexanecarboxylic acid methyl ester (250 mg, 1.12 mmol) and N-chlorosuccinimide (164 mg, 1.23 mmol) in N,N-dimethylformamide (2.2 ml) was stirred for 24 h at room temperature. The reaction mixture was partitioned between tert-butyl methyl ether (50 ml) and water (50 ml). The layers were separated. The aqueous layer was extracted with one 50 ml-portion of tert-butyl methyl ether. The combined organic layers were washed with one 50 ml-portion of 0.1 M aqueous sodium hydroxide solution, one 50 ml-portion of water and one 30 ml-portion of brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the crude title compound (275 mg, 95%) as light yellow oil, which was used in the next step without further purification. MS m/e: 257 (M+)

Workup

  1. customThe reaction mixture was partitioned between tert-butyl methyl ether (50 ml) and water (50 ml)
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted with one 50 ml-portion of tert-butyl methyl ether
  4. washThe combined organic layers were washed with one 50 ml-portion of 0.1 M aqueous sodium hydroxide solution, one 50 ml-portion of water and one 30 ml-portion of brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-773f7a7ed7e54c6dbefbeba401b7c5de
Source dataset
uspto-grants-2013_08
Patent number
US08513238B2

Reaction notes

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