Triphenylphosphine → HCID 86646579, compound
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC([O:24][CH:25]([CH3:27])C)=O.[Cl:34][C:35]1[N:40]=[CH:39][C:38]([CH2:41][N:42]([CH2:46][CH:47]([CH3:49])[CH3:48])[CH2:43][CH2:44]O)=[CH:37][CH:36]=1.[S:50]1C=CC=C1CC(O)=O>C1COCC1>[Cl:34][C:35]1[N:40]=[CH:39][C:38]([CH2:41][N:42]([CH2:46][CH:47]([CH3:49])[CH3:48])[CH2:43][CH2:44][S:50][C:25](=[O:24])[CH3:27])=[CH:37][CH:36]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
To a stirred, cold (0° C.) solution of 3.11 grams (0.012 mole) of triphenylphosphine in 200 mL of THF was added dropwise 2.28 grams (0.011 mole) of diisopropyl azodicarboxylate. The reaction mixture was stirred at 0° C. for five hours and at that time a solution of 1.37 grams (0.0056 mole) of 2-{[(6-chloro(3-pyridyl))methyl](2-methylpropyl)amino}ethan-1-ol and 0.94 gram (0.012 mole) of thiolacetic acid in 50 mL of THF was added dropwise. After complete addition the reaction mixture was stirred at 0° C. for one hour. The reaction mixture was concentrated under reduced pressure to a residue. The residue was purified by column chromatography on silica gel, eluting with mixtures of n-heptane and ethyl acetate. The appropriate fractions were combined and concentrated under reduced pressure, yielding 1.07 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.
Workup
- additionwas added dropwise
- additionAfter complete addition the reaction mixture
- concentrationThe reaction mixture was concentrated under reduced pressure to a residue
- customThe residue was purified by column chromatography on silica gel
- washeluting with mixtures of n-heptane and ethyl acetate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-d0c315c473f04727bb2d90814df7281d
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07932393B2
Reaction notes
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