Acetone → HCID 72808432, compound

HRID 1295547Notes

Reaction equation

HRID 1295547 reaction equation
[CH3:1][C@@H:2]1[C@H:20]([OH:21])[C@@H:19]([CH3:22])[C:17](=[O:18])[C:16]([CH3:24])([CH3:23])[C@@H:15]([OH:25])[CH2:14][C:12](=[O:13])[O:11][C@H:10](/[C:26](/[CH3:35])=[CH:27]/[C:28]2[N:32]=[C:31]([CH2:33][OH:34])[S:30][CH:29]=2)[CH2:9][C@@H:7]2[O:8][C@:6]2([CH3:36])[CH2:5][CH2:4][CH2:3]1.C[C@@H]1[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O[C@H](/C(/C)=C/C2N=C(C)SC=2)C[C@@H]2O[C@@]2(CO)CCC1.CC(C)=O>C1(C)C=CC=CC=1>[OH:25][CH:15]1[C:16]([CH3:24])([CH3:23])[C:17](=[O:18])[CH:19]([CH3:22])[CH:20]([OH:21])[CH:2]([CH3:1])[CH2:3][CH2:4][CH2:5][C:6]2([CH3:36])[CH:7]([O:8]2)[CH2:9][CH:10]([C:26]([CH3:35])=[CH:27][C:28]2[N:32]=[C:31]([CH2:33][OH:34])[S:30][CH:29]=2)[O:11][C:12](=[O:13])[CH2:14]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 9914741Epothilone FHCID 101942784HCID 101942784, compound

Product 1

HCID 72808432HCID 72808432, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

The latter mixture of epothilone F and 26-hydroxyepothilone B was refined further by column chromatography using a 700 ml gradient of toluene to 35% acetone in toluene. A total of twenty 35 ml fractions were collected. TLC analysis showed that fractions 14 and 15 contained pure epothilone F, while fractions 18 through 20 contained pure 26-hydroxyepothilone B. The total yield of epothilone F, calculated from the amount of epothilone F recovered (126.4 mg) to the amount of starting substrate, epothilone B (610 mg), was 20.7%.

Workup

  1. customA total of twenty 35 ml fractions were collected
  2. customrecovered (126.4 mg) to the amount

Sources & evidence

ORD record
ord-96cbcaa2d178443d904a376d3cbea3f2
Source dataset
uspto-grants-2007_07
Patent number
US07244594B2

Reaction notes

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