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

HRID 274899

反応式

HRID 274899 の反応式
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]

参加物

6

反応物 4

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

生成物 1

HCID 86748167Rhizoxin 3-iodopropionate収率 80.7%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-745364b5b29043b39a34a52823d2783a
出典データセット
uspto-grants-1995_02
特許番号
US05391564

関連ノート

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