Sulfuric Acid → Sanglifehrin A

HRID 1955303Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1955303
[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

Komponenten

4

Edukt 2

HCID 1118Sulfuric AcidHCID 22829433HCID 22829433, Verbindung

Produkt 1

HCID 5388925Sanglifehrin A

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-4bac1d281d634de9817fc4db8c461dbc
Quelldatensatz
uspto-grants-2000_09
Patentnummer
US06124453

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