Water → HCID 67247723, compound

HRID 410466Notes

Reaction equation

HRID 410466 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][C:9]([OH:17])([C:12]2[S:13][CH:14]=[CH:15][N:16]=2)[CH2:8][CH:7]1[CH3:18])=[O:5])[CH3:2].C1C(=O)N([Br:26])C(=O)C1.O.CCOC(C)=O>CN(C=O)C>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][C:9]([C:12]2[S:13][C:14]([Br:26])=[CH:15][N:16]=2)([OH:17])[CH2:8][CH:7]1[CH3:18])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 67247139HCID 67247139, compound

Product 1

HCID 67247723HCID 67247723, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the product of Step 1 (20 g, 74.3 mmol) in DMF (140 mL) was added NBS (15.9 g, 89 mmol). After the initial exotherm had subsided the reaction mixture was heated to 50° C. and stirred for 1 h. It was then cooled to room temperature and water (280 mL containing 7 g of sodium sulfite) was added followed by EtOAc. The layers were cut and the aqueous layer was back extracted with EtOAc (2×), and then the combined organics washed with H2O. The organic layer was dried with MgSO4, filtered and concentrated in vacuo. The crude residue was purified by flash chromatography to afford 4-(5-bromo-thiazol-2-yl)-4-hydroxy-2-methyl-cyclohexanecarboxylic acid ethyl ester (20 g, 57.4 mmol), MS ESI: [M+H]+ m/z 347.9.

Workup

  1. temperatureIt was then cooled to room temperature
  2. extractionthe aqueous layer was back extracted with EtOAc (2×)
  3. washthe combined organics washed with H2O
  4. dry with materialThe organic layer was dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-20a624adf54d44068566341b4e5c469f
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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