HCID 10109781, compound → HCID 9857840, compound

HRID 2086340Notes

Reaction equation

HRID 2086340 reaction equation
[OH:1][C@:2]([C:9]1[CH:14]=[C:13]([Si:15]([CH3:18])([CH3:17])[CH3:16])[N:12]=[C:11]([O:19][CH3:20])[C:10]=1[CH2:21][O:22]COC)([CH2:7][CH3:8])[CH2:3][C:4]([OH:6])=O>C(O)(C(F)(F)F)=O>[CH2:7]([C@:2]1([OH:1])[C:9]2[CH:14]=[C:13]([Si:15]([CH3:16])([CH3:17])[CH3:18])[N:12]=[C:11]([O:19][CH3:20])[C:10]=2[CH2:21][O:22][C:4](=[O:6])[CH2:3]1)[CH3:8]

Participants

3

Reactant 1

HCID 10109781HCID 10109781, compound

Product 1

HCID 9857840HCID 9857840, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a round bottom flask was added 9a (0.74 g, 1.99 mmol) followed by TFA (50 mL). The mixture was stirred at rt for 16 h and then concentrated under reduced pressure. The residue was dissolved in Et2O and neutralized with sat. NaHCO3. The organic phase was dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by flash chromatography (hexane-EtOAc 75:25) to yield 10a (0.43 g, 70%) with 90% ee as a white foam; [α]23D=+45.1 (c=0.86, CH2Cl2). Lactone 10a was analyzed for enantiomeric purity using a Chiralcel OD-H column with 92:8 hexane:iPrOH as the eluent, using the racemate as the standard.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in Et2O and neutralized with sat. NaHCO3
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by flash chromatography (hexane-EtOAc 75:25)

Sources & evidence

ORD record
ord-1be89ad4568240c4a064acca33a16d1c
Source dataset
uspto-grants-2004_04
Patent number
US06723853B2

Reaction notes

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