Propanoic acid, 3-iodo- → Rhizoxin 3-iodopropionate

HRID 1707269

Reaction equation

HRID 1707269 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.N1(C2C=CN=CC=2)CCCC1.[CH3:27][C:28]1[O:32][CH:31]=[C:30](/[CH:33]=[C:34](/[CH:36]=[CH:37]/[CH:38]=[C:39](/[C@H:41]([O:70][CH3:71])[C@H:42]([C@H:44]2[O:62][C:60](=[O:61])[C@@H:58]3[O:59][C@H:57]3[CH2:56][C@H:55]3[CH2:63][C:64]([O:66][C@H:53]([CH2:54]3)[C@H:52]([CH3:67])[CH:51]=[CH:50][C@H:48]3[O:49][C@:47]3([CH3:68])[C@@H:46]([OH:69])[CH2:45]2)=[O:65])[CH3:43])\[CH3:40])\[CH3:35])[N:29]=1.[I:72][CH2:73][CH2:74][C:75]([OH:77])=[O:76]>C1(C)C=CC=CC=1>[CH3:27][C:28]1[O:32][CH:31]=[C:30](/[CH:33]=[C:34](/[CH:36]=[CH:37]/[CH:38]=[C:39](/[C@H:41]([O:70][CH3:71])[C@H:42]([C@H:44]2[O:62][C:60](=[O:61])[C@@H:58]3[O:59][C@H:57]3[CH2:56][C@H:55]3[CH2:63][C:64]([O:66][C@H:53]([CH2:54]3)[C@H:52]([CH3:67])[CH:51]=[CH:50][C@H:48]3[O:49][C@:47]3([CH3:68])[C@@H:46]([OH:69])[CH2:45]2)=[O:65])[CH3:43])\[CH3:40])\[CH3:35])[N:29]=1.[I:72][CH2:73][CH2:74][C:75]([O-:77])=[O:76]

Participants

6

Reactant 4

HCID 8856Propanoic acid, 3-iodo-HCID 10868DicyclohexylcarbodiimideHCID 755674-PyrrolidinopyridineHCID 6437358Rhizoxin

Product 1

HCID 86748167Rhizoxin 3-iodopropionateYield 80.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.03 g of DCC and a catalytic amount of 4-pyrrolidinopyridine were added to a solution of 1.25 g of rhizoxin and 1.20 g of 3-iodopropionic acid in toluene, and the resulting mixture was stirred at room temperature for 2 hours. At the end of this time, the reaction mixture was treated in the same manner as described in Example 1, to give 1.33 g of rhizoxin 3-iodopropionate. The whole of this ester was immediately dissolved in 20 ml of acetonitrile, and 0.92 g of the silver salt of methylmercaptan prepared at the time of use was added. The resulting mixture was stirred at room temperature for 8 hours, after which the precipitate was filtered off. The solvent was then removed by distillation under reduced pressure, and ethyl acetate was added to the residue. The resulting mixture was washed with a 5% w/v aqueous solution of sodium bicarbonate and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, and the residue was purified by silica gel column chromatography, using a 1:1 by volume mixture of cyclohexane and ethyl acetate as eluent, to give 970 mg of the title product.

Workup

  1. additionAt the end of this time, the reaction mixture was treated in the same manner

Sources & evidence

ORD record
ord-26327fe3a74a4918adb457f31a517390
Source dataset
uspto-grants-1994_10
Patent number
US05352689

Linked notes

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