Acetic Acid → Benzoyl chloride

HRID 1796733Notes

Reaction equation

HRID 1796733 reaction equation
C[C:2]1[C@@H:19](OC([C@H](O)[C@@H](NC(C2C=CC=CC=2)=O)C2C=CC=CC=2)=O)[CH2:18][C@:14]2(O)[C:15](C)(C)[C:3]=1[C@@H:4]([O:59]C(C)=O)C([C@@]1(C)[C@H]([C@@H]2OC(C2C=CC=CC=2)=O)[C@]2(OC(C)=O)CO[C@@H]2C[C@@H]1O)=O.C(O)(=O)C.[Cl:67]CCl>C(OCC)(=O)C>[C:4]([Cl:67])(=[O:59])[C:3]1[CH:15]=[CH:14][CH:18]=[CH:19][CH:2]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 36314Paclitaxel

Product 1

HCID 7412Benzoyl chloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Before the C-4 sidechain can be added to the C-7 Cbz protected paclitaxel analog (9), the analog (9) must undergo protection of the 2-OH. The protection step is carried out by treating the reaction mixture containing analog (9) with an acid, preferably acetic acid to neutralize the reaction mixture. The dichloromethane in the neutralized reaction mixture is exchanged for ethyl acetate or other ester or amide organic solvent, and the resulting solution of 9 is treated with a strong base, preferably Li t-butoxide, and a benzoyl protecting agent, preferably benzoyl chloride, to form the 2-benzoyl (Bz) 7-hydroxy protected paclitaxel (10).

Workup

  1. additionby treating the reaction mixture

Sources & evidence

ORD record
ord-aa1ceb42baa74aaaafbfc89701da2053
Source dataset
uspto-grants-2006_04
Patent number
US07030253B2

Reaction notes

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