Triphenylphosphine → HCID 87976187, compound
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.O[CH:35]([CH2:47][CH2:48][CH3:49])[CH2:36][CH2:37][N:38]([CH3:46])[C:39](=[O:45])[O:40][C:41]([CH3:44])([CH3:43])[CH3:42].[C:50]([OH:58])(=[S:57])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>O1CCCC1>[CH3:42][C:41]([O:40][C:39](=[O:45])[N:38]([CH2:37][CH2:36][CH:35]([S:57][C:50](=[O:58])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[CH2:47][CH2:48][CH3:49])[CH3:46])([CH3:44])[CH3:43]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of triphenylphosphine (1.13 g, 4.32 mmol) in dry tetrahydrofuran (12 ml) was added diisopropyl azodicarboxylate (0.88 ml, 4.32 mmol) dropwise with stirring at 0° C. under nitrogen. After stirring for 0.5 h, a solution of (3-hydroxyhexyl)methylcarbamic acid, 1,1-dimethylethyl ester (500 mg, 2.16 mmol) and thiobenzoic acid (0.51 ml, 4.3 mmol) in dry tetrahydrofuran (10 ml) was added at 0° C. The reaction mixture was stirred at 0° C. for 1 h, and then stirred at room temperature overnight. The mixture was evaporated, the residue dissolved in toluene and eluted down a flash chromatography column using 10% ether/isohexane as eluent to give 420 mg (55%) of product as a pale yellow oil.
Workup
- stirringAfter stirring for 0.5 h
- stirringThe reaction mixture was stirred at 0° C. for 1 h
- stirringstirred at room temperature overnight
- customThe mixture was evaporated
- dissolutionthe residue dissolved in toluene
- washeluted down a flash chromatography column
Sources & evidence
- ORD record
- ord-d21319fd0db1415385ee8629f5b493f2
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06900243B2
Reaction notes
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