Ethyl Acetate → HCID 67247653, compound

HRID 1039951Notes

Reaction equation

HRID 1039951 reaction equation
[CH3:1][CH:2]([O:4][C:5]([CH:7]1[CH:12]([CH3:13])[CH2:11][C:10]([OH:19])([C:14]2[S:15][CH:16]=[CH:17][N:18]=2)[CH2:9][CH:8]1[CH3:20])=[O:6])[CH3:3].C1C(=O)N([Br:28])C(=O)C1.S([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O>CN(C=O)C.O>[CH3:3][CH:2]([O:4][C:5]([CH:7]1[CH:8]([CH3:20])[CH2:9][C:10]([C:14]2[S:15][C:16]([Br:28])=[CH:17][N:18]=2)([OH:19])[CH2:11][CH:12]1[CH3:13])=[O:6])[CH3:1]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24437Sodium SulfiteHCID 67184N-bromobutanimideHCID 67249435HCID 67249435, compound

Product 1

HCID 67247653HCID 67247653, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of the product of Step 2 (2.0 g, 6.7 mmol) in DMF (16 mL) was added NBS (1.38 g, 7.73 mmol) and the resulting solution heated to 55° C. After 60 min the reaction was cooled and a solution of sodium sulfite (500 mg) in water (30 mL) was added followed by EtOAc. The layers were separated, the aqueous layer was back extracted with EtOAc (2×). The combined organics were dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography to afford propan-2-yl-4-(5-bromo-1,3-thiazol-2-yl)-4-hydroxy-2,6 dimethylcyclohexanecarboxylate (2.2 g, 5.85 mmol) MS ESI: [M+H]+ m/z 375.9.

Workup

  1. temperatureAfter 60 min the reaction was cooled
  2. customThe layers were separated
  3. extractionthe aqueous layer was back extracted with EtOAc (2×)
  4. dry with materialThe combined organics were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-9dc0f81ff15e4b3186605b11696e92bf
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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