Sulfuric Acid → Sanglifehrin A

HRID 1955303ノート

反応式

HRID 1955303 の反応式
[CH3:1][CH2:2][C@@H:3]1[C:77](=[O:78])[NH:76][C@@:6]2([O:11][C@@H:10]([CH2:12][C@H:13]([OH:72])[C@H:14]([CH2:16][CH2:17]/[CH:18]=[CH:19]/[CH:20]=[C:21](/[C@H:23]3[O:58][C:56](=[O:57])[C@@H:54]4[NH:55][N:50]([CH2:51][CH2:52][CH2:53]4)[C:48](=[O:49])[C@H:47]([CH2:59][C:60]4[CH:65]=[CH:64][CH:63]=[C:62]([OH:66])[CH:61]=4)[NH:46][C:44](=[O:45])[C@H:43]([CH:67]([CH3:69])[CH3:68])[NH:42][C:40](=[O:41])[C@@H:32]4[CH2:33][CH2:34][C@:35]([O:38]C)([CH3:37])[O:36][C@@H:31]4[C@@H:30]([CH3:70])[C@@H:29]([OH:71])[CH:28]=[CH:27][CH:26]=[CH:25][CH2:24]3)\[CH3:22])[CH3:15])[C@H:9]([CH3:73])[C@H:8]([OH:74])[C@@H:7]2[CH3:75])[C@@H:5]([CH3:79])[CH2:4]1.S(=O)(=O)(O)O>C1COCC1.O>[CH3:1][CH2:2][C@@H:3]1[C:77](=[O:78])[NH:76][C@@:6]2([O:11][C@@H:10]([CH2:12][C@H:13]([OH:72])[C@H:14]([CH2:16][CH2:17]/[CH:18]=[CH:19]/[CH:20]=[C:21](/[C@H:23]3[O:58][C:56](=[O:57])[C@H:54]4[NH:55][N:50]([CH2:51][CH2:52][CH2:53]4)[C:48](=[O:49])[C@H:47]([CH2:59][C:60]4[CH:65]=[CH:64][CH:63]=[C:62]([OH:66])[CH:61]=4)[NH:46][C:44](=[O:45])[C@H:43]([CH:67]([CH3:68])[CH3:69])[NH:42][C:40](=[O:41])[C@H:32]([CH2:33][CH2:34][C:35]([CH3:37])=[O:38])[C@H:31]([OH:36])[C@@H:30]([CH3:70])[C@@H:29]([OH:71])[CH:28]=[CH:27][CH:26]=[CH:25][CH2:24]3)\[CH3:22])[CH3:15])[C@H:9]([CH3:73])[C@H:8]([OH:74])[C@@H:7]2[CH3:75])[C@@H:5]([CH3:79])[CH2:4]1

参加物

4

反応物 2

HCID 1118Sulfuric AcidHCID 22829433HCID 22829433、化合物

生成物 1

HCID 5388925Sanglifehrin A

試薬・触媒・溶媒 1

HCID 21881883Oxolane--water (1/1)溶媒

実験手順

A solution of 550 mg (0.50 mmol) of sanglifehrin C in 5 mL of 4:1 THF-water is treated with 0.5 mL of 2N aqueous sulfuric acid and stirred for 1.5 h. The reaction is quenched with saturated aqueous sodium bicarbonate and the resulting mixture is extracted twice with ethyl acetate. The organic solution is washed with saturated aqueous sodium bicarbonate solution and 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 (90:10 methyl-tert.-butyl ether:methanol) to yield sanglifehrin A as a white amorphous powder.

後処理

  1. customThe reaction is quenched with saturated aqueous sodium bicarbonate
  2. extractionthe resulting mixture is extracted twice with ethyl acetate
  3. washThe organic solution is washed with saturated aqueous sodium bicarbonate solution and 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 (90:10 methyl-tert.-butyl ether:methanol)

出典と根拠

ORDレコード
ord-4bac1d281d634de9817fc4db8c461dbc
出典データセット
uspto-grants-2000_09
特許番号
US06124453

反応ノート

読み込み中…