Sulfuric Acid → Sanglifehrin A

HRID 1955303Notes

Reaction equation

HRID 1955303 reaction equation
[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

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 22829433HCID 22829433, compound

Product 1

HCID 5388925Sanglifehrin A

Reagents, catalysts & solvents 1

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

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-4bac1d281d634de9817fc4db8c461dbc
Source dataset
uspto-grants-2000_09
Patent number
US06124453

Reaction notes

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