Synthesis of L-163007

Structure of L-163007

C34H38F3N5O6S

Principal investigator	Linda L. Chang
Publication year	1994
Synthesis type	Total
Number of steps	10 (3 parts)
References	J. Med. Chem. 1994, 37, 4464. US Patent 5,312,820 1994, 0. US Patent 5,281,514 1994, 0.

Part 1 of 3

intermediate structure

+

intermediate structure

Et3N

PhMe

50 to 95 °C, ON, 58%

intermediate structure

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Part 2 of 3

intermediate structure

t-BuNH2

CHCl3

RT, 12 h, 84%

intermediate structure

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intermediate structure

Pd(PPh3)2Cl2

DMF

90 °C, 5 h, 74%

See the Stille Coupling

intermediate structure

AIBN, NBS

CCl4

Reflux, 3 h, 78%

See the Wohl-Ziegler Reaction

intermediate structure

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Part 3 of 3

intermediate structure

+

intermediate structure

NaH

DMF

50 °C, 4 h, 92%

intermediate structure

ClF2CCO2Me, KF, CuI

DMF

120 °C, 12 h, 37%

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PtO2, H2

4 atm

EtOAc, EtOH

RT, 100%

intermediate structure

EtCOBr, DMAP

Pyr

RT, ON, 90%

intermediate structure

PhOMe

CF3CH2OH

RT, ON, 91%

intermediate structure

NaH, Boc2O

THF

50 °C, 22 h, 74%

intermediate structure

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