10-deacetylbaccatin III → HCID 86754576, compound

HRID 1738591Notes

Reaction equation

HRID 1738591 reaction equation
CC1[C@@H](O)[CH2:18][C@:14]2([OH:21])[C:15](C)(C)C=1[C@@H](O)C([C@@]1(C)[C@H]([C@@H:13]2OC(C2C=CC=CC=2)=O)[C@:11]2([O:33][C:34]([CH3:36])=O)[CH2:31]O[C@@H]2C[C@@H]1O)=O.C1(C)C=CC=CC=1.[CH3:47][I:48].CC(C)([O-])C.[K+:54]>O1CCCC1>[CH3:13][C:14]([CH3:18])([O-:21])[CH3:15].[K+:54].[CH3:47][I:48].[O:33]1[CH2:11][CH2:31][CH2:36][CH2:34]1

Participants

5

Reactant 3

HCID 15427210-deacetylbaccatin IIIHCID 23665647Potassium tert-butoxideHCID 86754574HCID 86754574, compound

Product 1

HCID 86754576HCID 86754576, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 10-deacetylbaccatin III (544 mg, 1 mmol) in a tetrahydrofuran/methyl iodide mixture (3/2, 5 ml) is added dropwise to a suspension of potassium t-butoxide (336 mg, 3 mmol, 3 equiv.) in tetrahydrofuran (4 ml) at -30° C. The mixture is then allowed to return gradually to room temperature. After stirring for 3 h 30, HPLC analysis indicates that the reaction mixture contains 10.0% (by internal standardization of the areas) of 7,10-dimethoxy-10-deacetylbaccatin.

Workup

  1. customto return gradually to room temperature

Sources & evidence

ORD record
ord-1df98d8599b34b56b7780b64264ff9a0
Source dataset
uspto-grants-1999_10
Patent number
US05962705

Reaction notes

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