Reaction equation
C(N(S(F)(F)[F:7])CC)C.[C:10]([O:14][C:15]([N:17]1[CH2:29][C@@H:28]([CH3:30])[N:27]2[C@H:19]([CH2:20][C:21]3[C:26]2=[N:25][C:24]([CH2:31]OCCO)=[CH:23][CH:22]=3)[CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]>ClCCl>[C:10]([O:14][C:15]([N:17]1[CH2:29][C@@H:28]([CH3:30])[N:27]2[C@H:19]([CH2:20][C:21]3[C:26]2=[N:25][C:24]([CH2:31][F:7])=[CH:23][CH:22]=3)[CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 82.0 μl (0.11 g, 0.63 mmol) diethylaminosulphur trifluoride in 2 ml dichloromethane was cooled to −78 deg C. and treated with a solution of 0.20 g (0.63 mmol) (4R,9aR)-6-(2-hydroxy-ethoxymethyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (Example 15, intermediate b) in 2 ml dichloromethane. The cooling bath was removed and the reaction stirred for 1 h at room temperature. The solution was extracted with 10% aqueous sodium bicarbonate solution, washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was chromatographed on silica gel (0.032–0.063 mm) with ethyl acetate:n-hexane (1:2) as eluant to afford the desired compound as a colorless oil (51.7%).
Workup
- customThe cooling bath was removed
- extractionThe solution was extracted with 10% aqueous sodium bicarbonate solution
- washwashed with brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customevaporated
- customThe residue was chromatographed on silica gel (0.032–0.063 mm) with ethyl acetate:n-hexane (1:2) as eluant
Sources & evidence
- ORD record
- ord-02cf394ff1174a2c8c2dd1ba46ed3904
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07098337B2
Linked notes
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