Methanol → HCID 22829433, 화합물

HRID 1955302노트

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HRID 1955302 반응식
[CH3:1][CH2:2][C@@H:3]1[C:76](=[O:77])[NH:75][C@@:6]2([O:11][C@@H:10]([CH2:12][C@H:13]([OH:71])[C@H:14]([CH2:16][CH2:17]/[CH:18]=[CH:19]/[CH:20]=[C:21](/[C@H:23]3[O:51][C:49](=[O:50])[C@H:47]4[NH:48][N:43]([CH2:44][CH2:45][CH2:46]4)[C:41](=[O:42])[C@H:40]([CH2:52][C:53]4[CH:54]=[CH:55][CH:56]=[C:57]([OH:59])[CH:58]=4)[NH:39][C:37](=[O:38])[C@H:36]([CH:60]([CH3:62])[CH3:61])[NH:35][C:33](=[O:34])[C@H:32]([CH2:63][CH2:64][C:65]([CH3:67])=[O:66])[C@H:31]([OH:68])[C@@H:30]([CH3:69])[C@@H:29]([OH:70])[CH:28]=[CH:27][CH:26]=[CH:25][CH2:24]3)\[CH3:22])[CH3:15])[C@H:9]([CH3:72])[C@H:8]([OH:73])[C@@H:7]2[CH3:74])[C@@H:5]([CH3:78])[CH2:4]1.[CH3:79]O>>[CH3:1][CH2:2][C@@H:3]1[C:76](=[O:77])[NH:75][C@@:6]2([O:11][C@@H:10]([CH2:12][C@H:13]([OH:71])[C@H:14]([CH2:16][CH2:17]/[CH:18]=[CH:19]/[CH:20]=[C:21](/[C@H:23]3[O:51][C:49](=[O:50])[C@@H:47]4[NH:48][N:43]([CH2:44][CH2:45][CH2:46]4)[C:41](=[O:42])[C@H:40]([CH2:52][C:53]4[CH:54]=[CH:55][CH:56]=[C:57]([OH:59])[CH:58]=4)[NH:39][C:37](=[O:38])[C@H:36]([CH:60]([CH3:61])[CH3:62])[NH:35][C:33](=[O:34])[C@@H:32]4[CH2:63][CH2:64][C@:65]([O:66][CH3:79])([CH3:67])[O:68][C@@H:31]4[C@@H:30]([CH3:69])[C@@H:29]([OH:70])[CH:28]=[CH:27][CH:26]=[CH:25][CH2:24]3)\[CH3:22])[CH3:15])[C@H:9]([CH3:72])[C@H:8]([OH:73])[C@@H:7]2[CH3:74])[C@@H:5]([CH3:78])[CH2:4]1

참가 물질

3

반응물 2

HCID 887MethanolHCID 5388925Sanglifehrin A

생성물 1

HCID 22829433HCID 22829433, 화합물

실험 절차

To a stirred, cooled (0° C.) solution of 20 mg (18.3 μmol) of Sanglifehrin A in 0.5 mL of methanol is added one crystal of paratoluenesulfonic acid monohydrate. The resulting yellow solution is stirred for one hour and the reaction is quenched with saturated aqueous sodium bicarbonate solution. The resulting mixture is extracted twice with ethyl acetate. The organic solution is washed twice with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (95:5 methyl-tert.-butyl ether:methanol) to yield Sanglifehrin C as a white amorphous powder. The latter consisted of a 4:1 mixture of Sanglifehrin C and its C53 epimer, Sanglifehrin C having the (S) configuration as depicted below (R=Me). ##STR53##

후처리

  1. customthe reaction is quenched with saturated aqueous sodium bicarbonate solution
  2. extractionThe resulting mixture is extracted twice with ethyl acetate
  3. washThe organic solution is washed twice with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by column chromatography on silica gel (95:5 methyl-tert.-butyl ether:methanol)

출처 및 근거

ORD 기록
ord-b2187ee870934d4eb9930fc54d8ab738
출처 데이터셋
uspto-grants-2000_09
특허 번호
US06124453

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