Tamibarotene synthesis
2synthesis methods
- Product Name:Tamibarotene
- CAS Number:94497-51-5
- Molecular formula:C22H25NO3
- Molecular Weight:351.44
Several synthesis of tamibarotene have been disclosed
in the literature including the process scale synthesis
as shown in the scheme. The synthesis started
with preparation of dichloride 134 in 82% yield from diol
133 by treating with concentrated HCL in DCM. Friedal
Crafts reaction of dichloride 134 with acetanilide in the presence
of aluminum chloride at -15°C for 2h provided
acetanilide derivative 136 in 78% yield. In a single pot, the
acetanilide was reacted with PCl5 and dimethylaniline at -25°C for 1.5h followed by quenching the reaction with
methanol for 2h after addition at -25°C. Addition of dimethylaniline
and terepthalic chloride mono-methylester at -30 - -
20°C for 1 hr provided the tamibarotene methyl easter 137 in
81% yield. Hydrolysis of the ester by heating with sodium
hydroxide in MeOH:water mixture for 1h followed isolation
and crystallization gave tamibarotene (XIX) in 92% yield.
1446134-13-9
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