Triphenylphosphine → HCID 10575424, compound
Reaction equation
[CH3:1][CH:2]([CH:9]1[C:13]2([CH3:30])[CH:14]([OH:29])[CH2:15][CH:16]3[C:21]4([CH3:27])[CH2:22][CH2:23][CH:24](O)[CH2:25][CH:20]4[CH2:19][CH:18]([OH:28])[CH:17]3[CH:12]2[CH2:11][CH2:10]1)[CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P([N:64]=[N+:65]=[N-:66])(C2C=CC=CC=2)=O)C=CC=CC=1>C1COCC1>[CH3:8][O:7][C:5](=[O:6])[CH2:4][CH2:3][C@H:2]([C@@H:9]1[C@:13]2([CH3:30])[C@H:12]([C@H:17]3[C@H:16]([CH2:15][C@@H:14]2[OH:29])[C@:21]2([CH3:27])[C@@H:20]([CH2:25][C@@H:24]([N:64]=[N+:65]=[N-:66])[CH2:23][CH2:22]2)[CH2:19][C@H:18]3[OH:28])[CH2:11][CH2:10]1)[CH3:1]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2.06 g of cholic acid methyl ester (marketed product) (4.87 mmol), 1.28 g of triphenylphosphine (4.88 mmol) and 1.70 g of diethylazadicarboxylate (0.76 mL, 4.88 mmol) in 50 ml of THF, at room temperature and under inert atmosphere, was added to a solution of 1.4 g of diphenylphosphorylazide (1.1 mL, 5.11 mmol) in 5 ml of THF during 15 minutes. After 24 hours at room temperature, 1 equivalent of diethylazadicarboxylate (0.76 mL, 4.88 mmol) and 1 equivalent of triphenylphosphine (1.28 g, 4.88 mmol) were added. After a further 24 hours the solvent was evaporated off under reduced pressure and the resulting crude was purified by flash chromatography. 1.6 g of the desired product (3.57 mmol) was obtained.
Workup
- customAfter a further 24 hours the solvent was evaporated off under reduced pressure
- customthe resulting crude was purified by flash chromatography
Sources & evidence
- ORD record
- ord-10d18157e01e4cb59b52850235638148
- Source dataset
- uspto-grants-1997_07
- Patent number
- US05649537
Reaction notes
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