Ethyl Acetate → HCID 67247653, compound

HRID 410468Notes

Reaction equation

HRID 410468 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 58.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of the product of Step 2 (1.4 g, 4.7 mmol) in DMF (15 mL) was added NBS (0.963 g, 5.41 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 twice with EtOAc and the combined organics were dried with 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 (1.04 g, 2.76 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 twice with EtOAc
  4. dry with materialthe combined organics were dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-b535212a2194423dbf77b20a3f3edd5c
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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