Acetone → HCID 178458903, compound

HRID 1158094Notes

Reaction equation

HRID 1158094 reaction equation
[C@@H:1]12[CH2:7][C@@H:4]([CH2:5][CH2:6]1)[CH2:3][C@@H:2]2[NH:8][C:9]1[S:10][CH:11]([CH3:15])[C:12](=[O:14])[N:13]=1.[Li+].CC([N-]C(C)C)C.[CH3:24][C:25]([CH3:27])=[O:26]>C1COCC1>[C@@H:1]12[CH2:7][C@@H:4]([CH2:5][CH2:6]1)[CH2:3][C@@H:2]2[NH:8][C:9]1[S:10][C:11]([C:25]([OH:26])([CH3:27])[CH3:24])([CH3:15])[C:12](=[O:14])[N:13]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 2724682Lithium diisopropylamideHCID 178435107HCID 178435107, compound

Product 1

HCID 178458903HCID 178458903, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 2-((1S,2S,4R)-bicyclo[2.2.1]heptan-2-ylamino)-5-methylthiazol-4(5H)-one (1.10 g, 5.0 mmol) in THF (5 ml) at −78° C. was added LDA (2.0 M, 10 ml). After 5 min, acetone was added, and the reaction mixture was stirred for 1 h at −78° C. The resulting reaction mixture was poured into a sat'd NaH2PO4, and extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The crude residue was purified by flash chromatography (4:1; Hexane:EtOAc) to give the title compound as a white solid. MS (ES+): 283 (M+H)+. The diastereomers were separated using standard HPLC methods described within this text.

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by flash chromatography (4:1; Hexane:EtOAc)

Sources & evidence

ORD record
ord-f9e25101822c426db4338ca4525a62f0
Source dataset
uspto-grants-2010_10
Patent number
US07807700B2

Reaction notes

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