Methanol → HCID 22829433、化合物

HRID 1955302ノート

反応式

HRID 1955302 の反応式
[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

参加物

3

反応物 2

HCID 887MethanolHCID 5388925Sanglifehrin A

生成物 1

HCID 22829433HCID 22829433、化合物

実験手順

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##

後処理

  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)

出典と根拠

ORDレコード
ord-b2187ee870934d4eb9930fc54d8ab738
出典データセット
uspto-grants-2000_09
特許番号
US06124453

反応ノート

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