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

HRID 274899

반응식

HRID 274899 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

HCID 86748167Rhizoxin 3-iodopropionate수율 80.7%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-745364b5b29043b39a34a52823d2783a
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05391564

연결된 노트

불러오는 중…